100 Fun Things to Do in Chicago

Chicago is one of the largest cities in the United States and its cultural influence is significant throughout the Midwest. I invite you to get to know it under the recommendations I have prepared for you of the most interesting places in this great American metropolis.

Keyvis Montilva

Keyvis Montilva

62 min read

100 Fun Things to Do in Chicago

Chicago | Paisaje urbano de Chicago ©Pixabay

Are you going to travel soon to the United States and the city of Chicago is going to be one of the stops in your tourist itinerary? Well let me assure you that this is going to be one of the best experiences of your life, as this great city of over 9 million inhabitants is one of the tourist epicenters of all North America.

With these attractions and activities that I have highlighted for you, you will be able to enjoy a pretty complete look of this beautiful community and at the same time give you the opportunity to keep yourself entertained from the first moments of your trip, until that last moment when you find yourself leaving your hotel on a transfer to the Chicago airport.

1. Participate in a guided tour of the downtown area

people walking in the garden| ©RockledgeGardens
people walking in the garden| ©RockledgeGardens

Being such a large city with so much history, it is predictable that there are plenty of Chicago tour alternatives for those who are interested in learning about this community in a more personalized and conventional tourist mode.

Most of these guided tours will take you to the most important sites downtown and this is convenient due to the fact that this is the area with the most tourist traffic. So having an itinerary that fits the knowledge of the experts can save you a couple of detours and a lot of time.

At the same time, you have to understand that the modalities offered by these tours are very different and there is a huge repertoire for tourists with all kinds of interests. For example, the mobster and gangster tours are some of the most entertaining of the local offer, as it is a tour that takes you to the corners that became crime scenes during the times when the mafia took over this city.

Some tours are in tour buses and others in minibuses, but you also have the option of going to know the city from the heights with the spectacular helicopter tours of Chicago.

Details of interest:

  • Prices: prices are another favorable issue of these guided tours, since on average they cost between about 25 to 40 euros per person, although helicopter flights logically tend to have higher prices.
  • Duration: it all depends on the chosen itinerary, but they vary between 3 and 5 hours, although this estimate is only an approximation.

Book the best tours in Chicago

2. Tour the shores of Lake Michigan and the banks of the Chicago River on a cruise

people on a boat on Lake Michigan| ©Thomas Shockey
people on a boat on Lake Michigan| ©Thomas Shockey

Chicago is located just at the southern end of Lake Michigan, one of the 5 bodies of water that make up the Great Lakes system that are distributed between the border of Canada and the United States. The city's skyline has grown along this coastline and therefore it is an excellent idea to spend some time during your visit touring some of the sites that this community has created to enjoy the waters of one of the largest lakes in the world.

North Avenue Beach is one of the favorite places if you are looking for beach fun on a summer day, while The Concrete Beach is an extension of that promenade, but with less vegetation that can be an ideal place for a bike ride.

The Navy Pier is another stop you can not miss if you want to tour the shore of Lake Michigan on your visit to Chicago. This pier was one of the longest in the world for many years and today has several attractions such as the Chicago Children's Museum that joins a lot of stores and public parks with free admission.

As for the Chicago River you have to know that this is one of the most interesting waterways on the planet. In the 19th century its waters were redirected thanks to a large-scale civil engineering project that allowed it to flow in a southerly direction, thus avoiding the pollution of Lake Michigan.

Riverwalk is the path that has been conditioned so that pedestrians can enjoy the banks of the river in a good part of its passage through the center of the city and the recommendation I can make is that you walk it from the bridge section of Columbus Dr. N to the Franklin-Orleans Street Bridge.

But there are also cruises that tell you the history of Downtown, while highlighting the relevance of each of the skyscrapers and elevated bridges in the area. While cruises with tours of Lake Michigan are other entertainment alternatives highly recommended after a morning of touring the urban heart of the city.

  • Read more... If you want to know more about water rides in Chicago, check out this article about cruises on Lake Michigan.

Book a cruise on Lake Michigan

3. Experience an afternoon full of art at the Chicago Art Institute

man posing in a colorful mural| ©Chait Goli
man posing in a colorful mural| ©Chait Goli

Right next to Millennium Park is the Art Institute of Chicago. This is an important institution in the global art world, both for the breadth of its repertoire of works as well as for the relevance that some of them have within the interpretative currents to which they belong.

American Gothic by Grant Wood, Afternoon on the Island of Grande Jette by Seurat and Van Gogh's self-portrait are just some of the great protagonists of this museum. It has the largest number of visitors of any museum in the city, reaching an impressive 1.5 million admissions annually.

The collection spans different branches of art history ranging from American art to a strong display of Byzantine works, as well as African art and contemporary and modernist works.

Other iconic buildings such as the Chicago Symphony Orchestra are on the perimeter near this museum. The truth is that it is not a bad idea to get your tickets through some of the Chicago tourist attraction passes and enjoy the Best Chicago Museums.

One of these tourist passes, the Chicago Explorer Pass, includes, for example, tickets to the Museum of Contemporary Art Chicago, and also access to the 360 Observation Deck in Chicago, two of the must-see attractions in the city.

Book a visit to the Art Institute of Chicago

4. Take in the panoramic view of the city from the Willis Tower

buildings under the blue sky| ©Otto Rascon
buildings under the blue sky| ©Otto Rascon

The Willis Tower represents a place that is automatically associated with the architectural identity of Chicago, due to the fact that this 110-story skyscraper became the tallest building in the world for a couple of years. To this day it remains the king of the skies in this city and although it stopped being called Sears Tower to be officially known as Willis Tower, it has not ceased to be an important space for this community.

You have the opportunity to get to know this building in a very particular way, because on the 103rd floor there is a viewpoint that allows you to stand on glass cubes that will leave you standing in a literal way over the panorama of the city.

The viewpoint is known as Skydeck and the glass cornices are called The Ledge. On a day with favorable weather you will have the opportunity to see absolutely the entire city in a panoramic fashion and your visibility will extend all the way to the well-known suburbs of the Chicago Metropolitan Area.

Details of interest:

  • Pricing: Ticket prices for the Willis Tower Skydeck are usually around €30 per adult and €20 or €25 per child. I advise you to buy your tickets in advance if you want to guarantee a space for the hours you have available for this activity in your day.
  • Hours: It is open every day of the week and its hours extend until 9:00 pm. Which is logical knowing that enjoying this beautiful view is one of the best things to do in Chicago at night if you are talking about a plan with a fairly family oriented approach.

Book a visit to the Chicago Skydeck at Willis Tower

5. Take a guided tour of Chicago by segway

people on segway| ©ivecanski
people on segway| ©ivecanski

If you want to admire the Museum Campus and the Chicago Lake, this guided segway tour is a good option. You don't have to walk, you just ride an electric skateboard, but with this comfortable vehicle you enjoy the same visits as when you go on foot.

An expert guide will be telling you stories and curious facts about the city or the places where you will pass. You will have a segway tour of 7 or 8 miles to visit various sites such as Soldier Field, the home of the Chicago Bears.

Book a guided segway tour in Chicago

6. Fly over Chicago in a private helicopter

Chicago from the air| ©Karl Solano
Chicago from the air| ©Karl Solano

Taking a helicopter ride and gazing at the Chicago skyline is a must-do if you're visiting the trendy city. This tour lasts 45 minutes, which is more than enough time to take some epic photos.

Also, you should know that the tour includes noise-reduction headphones and commentary from a guide. Also, please note that this tour is a good option for 3 passengers, so you can go with your family or friends.

  • Know more... If you want to know more about this kind of activity, check out this article of best helicopter tours.

Book a helicopter tour in Chicago

7. Buy the Chicago CityPASS and get access to several impressive sites

Chicago CityPASS| ©Jeff Keenan
Chicago CityPASS| ©Jeff Keenan

In case you didn't know, the Chicago CityPASS offers admission to various tourist sites in the city. For example, Skydeck Chicago, Shedd Aquarium, Field Museum and other sites. The goal of this pass is to save up to 50% on admission to fairly crowded sites.

Other sites you can visit with this pass are Chicago 360 Observatory and Art Institute of Chicago. You even have the option to visit the Adler Planetarium, one of the most recommended sites for the whole family, including children.

Purchase the Chicago CityPASS

8. Take a minibus tour of Chicago

two white minibuses| ©Paul Hills
two white minibuses| ©Paul Hills

If you want to see Chicago highlights on a minibus, this might be the most recommended option for you. This is a small group tour with stops at prominent tourist sites. Bring your camera or drone to take exciting photos and videos.

Among the sites you will see are: The Rookery skyscrapers, Millennium Park, Museum Campus, Buckingham Fountain, Magnificent Mile, Chicago River, Lincoln Park and Gold Coast. You will definitely have a great time with a local guide who will tell you interesting facts about the city.

Book a minibus tour of Chicago

9. The Field Museum is another of the great wonders of the city

Skeleton of the Museum| ©tagbuzzard
Skeleton of the Museum| ©tagbuzzard

Continuing the idea that the Museum Campus area is an ideal place for a sightseeing itinerary in this beautiful city, the Field Museum of Natural History in Chicago stands out. It is known for the fact that inside is exhibited the largest Tyrannosaurus Rex unearthed to date and is therefore an unmissable stop for lovers of the curiosities of our planet earth.

It really is one of the largest museums in the world in terms of the breadth of its exhibits and the type of approaches that are handled from the curatorship. For there you will learn about the different ecosystems that make up life on the planet, while also accessing the occasional exhibition of articles from the history of ancient and modern societies.

Details of interest:

  • Prices: If you are interested in buying tickets to the Field Museum of Natural History in Chicago, you have to know that the rates are around 30 euros per adult for a general admission and 36 or 38 euros for an access that allows you to simultaneously enjoy the 3D cinema that is in this facility. Children between 5 and 18 years have a discount of approximately 10%.

  • Hours: Open daily from 9 am to 5 pm. Keep in mind that it will take you approximately 4 hours to go through all the exhibits.

  • Learn more... If you want to know more about this activity, read the article tickets to the Field Museum of Natural History.

Book a visit to the Field Museum of Natural History

10. Enjoy an authentic gastronomic tour of the city

pizzas on display| ©Annija Mieze
pizzas on display| ©Annija Mieze

Every city begins to develop a unique gastronomic universe as the years go by. They also do so according to the historical and cultural events that mark the growth of society in the sense of community. In the case of Chicago something quite interesting happens, as it is a very authentic and unique blend of Italian, American and Irish gastronomy that occurred as a consequence of the mix of these populations in this beautiful city.

Eating Chicago style pizza, tasting some Hot Dogs under the interpretation given by the locals and sitting in a bar to drink an authentic Irish beer, are some of the activities that could be part of these gastronomic tours of the city. Which can come in a lot of modalities for all types of tourists.

For example, there are some tours that are focused exclusively on getting to know the best donut shops in the city, while others combine a tourist cycling route with stops at the most iconic restaurants in the area where they are located. As long as they are dedicated to preparing these meals that have been enhanced with Chicago's gastronomic flair.

Keep in mind that most of Chicago' s best food tours tend to occur in the early morning or after noon, as well as prices vary depending on the type of activity being undertaken. Clearly, tours that include you renting a bike along with a couple of gastronomic stops tend to have higher rates than a walking tour that only focuses on a perimeter of 2 or three kilometers around.

Details of interest:

  • Prices: It all depends on the type of tour chosen, but on average they can vary between 20 or 60 euros depending on the number of stops and whether or not they include the meals advertised in the itinerary.

  • Duration: It is not common for a gastronomic tour to last more than three hours, but it is not usual for them to last less than 1 hour.

  • Learn more... If you want to know more about the best food in the city, check out this article on food tours in Chicago.

Book a food tour in Chicago

11. Admire the city's architecture while strolling along the Chicago River

boats on the river with a view of the buildings| ©Victor Silas
boats on the river with a view of the buildings| ©Victor Silas

A ride on the great Chicago River will allow you to admire the urban architecture from a natural setting with your family, including children, who will also be fascinated by the natural environment and the beautiful views. In addition, on this tour you will enjoy commentary from an architectural expert, so you will learn about the historical aspects of the site.

Some of the impressive buildings you will see include Willis Tower, Tribune Tower and John Hancock Center. In other words, you will see 100-story skyscrapers for you to take unforgettable photos and post them on Instagram and other social networks. Keep in mind that this tour lasts 1 hour and 15 minutes, so you can go to other tourist sites on the same day.

Book a ride on the Chicago River

12. Stop at Union Station

Train Station| ©Luis Leon
Train Station| ©Luis Leon

If you love historic buildings and have a passion for all things railroad related then you have to visit Union Station. It is the most important station in the United States public rail system for the Midwest region and its internal car storage configuration is so large that it extends subway through 9 city streets.

The structure of the building is quite iconic and for this simple reason it is already an interesting destination in your tourist planning. The marble floors, wide staircases and neo-classical finishes of its architecture also makes it one of the last spaces that adequately preserve the beauty of the American railway stations of the last century.

In turn, if you are traveling in the month of December, this is a very suitable place to include in your plans to see and do in Chicago during Christmas. This is due to the fact that it is a space that is decorated under all the splendor of Christmas aesthetics and this makes it an ideal place for a first class photo shoot.

13. Go for a night ride on a BIGBUS in Chicago

bigbus at night| ©Matt Taylor
bigbus at night| ©Matt Taylor

The BIGBUS features a roofless second deck, so you can get a better view of the city at night and enjoy the lights of the stores and impressive skyscrapers. Note that the BIGBUS passes by the Campus Museum, from where you can see Chicago's illuminated skyline.

One of the stops is the Tribune Tower, for beautiful views at sunset. Another site of the tour is The Magnificent Mile, one of the largest avenues in the United States. In addition, you should know that the bus has audio commentary in English.

Book a ticket for Chicago's Big Bus

14. Travel around Lake Michigan on a speedboat

speedboat on the lake| ©West Osee
speedboat on the lake| ©West Osee

I invite you to board a 2,000 horsepower speedboat to tour the wide and beautiful Lake Michigan. This is an activity that mixes natural landscapes and incredible urban views of the city of Chicago.

Also, a guide will give you entertaining descriptions of Chicago as you speed along in the boat. This speedboat ride lasts 30 minutes and allows you to see The Magnificent Mile, Buckingham Fountain, Navy Pier, among other sites.

Book a speedboat tour on Lake Michigan

15. Drink delicious Chicago craft beers

people with beer in hand| ©Oleksandr Pidvalnyi
people with beer in hand| ©Oleksandr Pidvalnyi

This is one of my favorite tours in Chicago, as I love the taste of craft beer. Thanks to this tour you can visit the most outstanding breweries in Chicago. Among them, I can mention a craft beer production company, so you can see how this delicious beverage is prepared.

In total, this tour offers the visit of 3 popular breweries in the windy city. In addition, the package includes 45 to 55 ounces of craft beer and a bus shaped like a keg of beer. Do you like beer? In Chicago you'll taste great local brews.

Book a Chicago Craft Beer Tour

16. Visit "The Loop" and hear incredible stories of ghosts and mobsters

The Loop| ©Ken Yuel
The Loop| ©Ken Yuel

The Loop district of Chicago has a lot of history, for example, several local mobsters have passed through the Loop and left their mark on the city. You will learn stories and anecdotes of gangsters and ghosts, two topics at a low cost.

Likewise, a guide will tell you spooky stories of the district and show you several haunted sites that you will never forget. Without a doubt, this is an activity you can enjoy at any time of the year.

Book a ghost tour of The Loop

17. Cheer on your Chicago White Sox Team

Aerial view of baseball stadium| ©|=_=|
Aerial view of baseball stadium| ©|=_=|

Attend a Major League Baseball game with perhaps your favorite team, the Chicago White Sox. Clap and yell in support of your MLB team; the excitement amidst thousands of baseball fans is breathtaking.

All games are held at Guaranteed Rate Field, the home stadium of the Chicago White Sox. Not only will you see your team play, but you'll also see their MLB rivals, depending on the ticket you purchase. What are you waiting for? Buy Chicago White Sox tickets in advance to see this MLB team playing in their hometown.

Book Chicago baseball tickets

18. Visit Millennium Park and see the world famous Cloud Gate

metal structure under the blue sky| ©Adam Bernstein
metal structure under the blue sky| ©Adam Bernstein

Chicago is a city that is internationally known for the breadth of its green spaces and for the modernity that characterizes these public parks. Millennium Park is one of the most iconic of them all and its proximity to the financial and tourist epicenter of the city makes it a main stop on your first days of your trip.

It was inaugurated in 2004 and since then its 10 hectares full of modern and abstract sculptures are presented as an entrance to what has become the Downtown of the city.

There you will find all kinds of iconic elements of architecture and art, leaving as a great protagonist of the place the concert pavilion that was designed by the talented architect Frank Gehry. If you're lucky, you're likely to catch a band playing live music for the simple fact that this public space tries to remain an interesting place for tourists and locals alike.

However, the attraction that undoubtedly steals all eyes at this site is the Cloud Gate sculpture, which was designed by Anish Kapoor and is now known as The Bean for its curious structure that resembles that of a giant, reflective metallic bean.

Keep in mind that admission to this beautiful corner of the city is completely free. In addition, its proximity to the urban epicenter of this metropolis makes it an excellent plan to do in the morning and continue a tour of the skyscraper area of the Chicago River.

As this park is located right on the axis of public spaces that extend for several miles along the shore of Monroe Harbor, it is also advisable to participate in the best Segway tours in Chicago.

These state-of-the-art scooters can take you from Millennium Park to Buckingham Fountain or Grant Park, which are other beautiful sites worth visiting on a morning of walking in the fresh air.

Book a Chicago Segway Tour

19. Stop by the Adler Planetarium

Adler planetarium| ©Logan Selinski
Adler planetarium| ©Logan Selinski

The Adler Planetarium is another of the most important institutions in the country and curiously is the oldest planetarium in the United States. It was inaugurated in 1930 and nowadays it combines technological shows about outer space with permanent exhibitions of old astronomy instruments and all kinds of books about this interesting branch of science.

There are also exhibitions about the Apollo 11 moon landing and if you wish, you can go back to the beginning of the last century to see how the Chicago sky looked like before the excess of light pollution that characterizes the great modern metropolis.

Clearly, it is one of the best activities to see or do in Chicago with children because of the educational potential of an experience like this. As well as for the fun it can be for the whole family.

Its location on the shores of Lake Michigan is also privileged, since it is in the same area of public parks where the Shedd Aquarium and the Field Museum of Natural History are located. Both of which are other family entertainment alternatives that you can visit on other days of your trip or that you can even visit on the same date if you organize yourself so that one is behind the other in your tourist planning.

Details of interest:

  • Prices: prices range from 20 to 35 euros per adult depending on the number of audiovisual shows to which you have access. The cheapest ticket only includes admission to the planetarium museum.
  • Hours: open every day of the week from 9 am to 9 pm except on Wednesdays that extends its opening until 10 pm. There are special hours during peak tourist seasons.

20. Marvel at the beauty of the Chicago Theatre

View of the Chicago Theatre| ©Antonio Intini
View of the Chicago Theatre| ©Antonio Intini

If you've done a little research on theaters that are influential to popular culture, you've probably come across a couple of images of the Chicago Theater. Its recognizable vertical sign with the name of the city reaches 20 feet high and over the decades has become an emblem of the identity of this beautiful metropolis.

It is over 100 years old and at the time of its creation it functioned as a movie theater to show silent films. The passage of time turned it into a more complete space and today it is used for the staging of theatrical projects, as well as live concerts.

You can get to know it with some of the guided tours that are given every noon, which is a good opportunity to learn firsthand about the secrets that have been kept in this building since the times when artists like Frank Sinatra performed in massive functions inside.

You also have the option of experiencing a live show. In addition, something very convenient is that the theater's official website announces its schedule of events several months in advance. At the same time, the perfect climate control of this amazing establishment also makes seeing a show one of the best things to do in Chicago during the winter if you are fleeing the cold temperatures of the Windy City.

21. Book a bus with free stops around Chicago

Tour People| ©Dan Gaken
Tour People| ©Dan Gaken

A hop-on hop-off bus tour could not be missing on your Chicago bucket list, as you have the opportunity to visit the sites you want, for example, Chicago River, Willis Tower, Adler Planetarium and Cloud Gate. You decide whether you purchase a Deluxe, Premium or Classic ticket, each option has its advantages.

Also, keep in mind that you can stop at Millennium Park, Skydeck Chicago, Water Tower and Magnificent Mile, so this is a pretty complete tour of the city of Chicago.

Book a bus with free stops in Chicago

22. Go to a Chicago Cubs game

Chicago cubs ticket| ©Shutter Runner
Chicago cubs ticket| ©Shutter Runner

When you go to Chicago don't forget to visit the major league baseball stadium Wrigley Field, especially if you would like to see a Chicago Cubs game. This baseball stadium was built in 1914 and has a capacity of 41,160 for games and 41,847 for concerts.

The Chicago Cubs play other MLB teams throughout the year, but you should check available dates and plan your visit accordingly. If you want to learn more about Chicago Cubs tickets, check out upcoming games.

Book Chicago Cubs tickets

23. See the city from a 360° observation deck

people at the observatory| ©Mike Steele
people at the observatory| ©Mike Steele

In Chicago there is an incredible observation deck from where you can see much of the city in 360°. Thus, it is a favorite activity for lovers of epic selfies. By the way, the formal name of this site is John Hancock Observatory.

From the observatory you can enjoy beautiful views and contemplate the Chicago skyline. In addition, you can opt for an exemplary view of the city from a tilting platform (TILT). This last option is 305 meters high.

24. Dine on a dinner cruise and enjoy incredible views in Chicago

people seated at the dinner cruise table| ©Kelly
people seated at the dinner cruise table| ©Kelly

This is a 3-course dinner on Lake Michigan. Plus, the dinner takes place on a beautiful Chicago cruise ship, so you can admire the architecture of the place while sharing a delicious meal with your loved ones.

In addition to dinner, the package includes unlimited hot or cold tea, water and coffee. This way, you won't have to carry drinks with you to quench your thirst or warm up your body. In addition, the average duration of the cruise is 2.5 hours.

Book the dinner cruise in Chicago

25. Cycle around the city of Chicago on a bike tour

two people biking by the lake| ©Chait Goli
two people biking by the lake| ©Chait Goli

With this tour you can pedal up to 22 km through the Windy City. Also, the tour includes stops at craft breweries and high quality local food stores. In other words, in just 4 hours you will be able to taste a variety of Chicago dishes and beers.

Some of the places you will visit are The Wiener's Circle, Murphy's Bleachers and Half Acre Bear Company. The package includes admission to these and other sites, so you won't have to spend extra money on different tickets. You only have to pay for admission to Wrigley Field.

Book a Chicago Bike Tour

26. Enjoy the fascinating Art Deco Chicago

two buildings with a view from below| ©Irina Hynes
two buildings with a view from below| ©Irina Hynes

Walk around the city in the company of a professional guide to observe the incredible Art Deco buildings or skyscrapers. This is because Chicago is one of the few cities that promotes the Art Deco movement in the world.

For example, you can enjoy the 1920's Jazz Deco and Modern Art buildings of Chicago. Likewise, the tour includes admission to the Chicago Architecture Center, where you can see several architectural galleries.

Book an Art Deco tour of Chicago

27. Have a BYOB Spray experience with The Studio W.I.P

man painting a picture| ©Leon Keay
man painting a picture| ©Leon Keay

The Studio W.I.P. offers you a street painting experience that opens your mind and helps you unleash all the creativity you have inside. The school provides you with a workshop with local artists in which you can create your own work.

In this way, using aerosols or stencils you will create your BYOB painting together with a teacher or expert guide. At the end of the workshop you can take your artwork home. The workshop includes the materials to paint and the canvas you will take with you.

Book a street art workshop in Chicago

28. Learn about historical aspects of literature at the American Writers Museum.

People viewing paintings on the wall| ©Rasande Tyskar
People viewing paintings on the wall| ©Rasande Tyskar

Learn about the history of poets and sportswriters, as well as their places of origin. Also, learn about the houses affiliated with this museum at Writers Hall. And other things you should explore are the galleries such as Wintrust Chicago and The Mind of Writers.

In the Wintrust Chicago gallery you will find important facts about local writers and their literary style. Also, you should check out the Tools of the Trade gallery, where you will find various tools used by famous writers.

Book tickets for the American Writers Museum

29. Taste the most delicious pizzas in Chicago

Entrance to the pizzeria| ©Matt
Entrance to the pizzeria| ©Matt

Are you really a pizza lover? Well, through this tour you will be able to get to know different favorite pizzerias in Chicago. For example, Pizano's Pizza and Flo & Santo's, two mythical local pizzerias. As a curious fact, the first one is active since 1943.

Another pizzeria you can get to know through this gastronomic tour is Pequod's, a pizza legend, thanks to the caramelized cheese topping. You can also visit Coalfire, a place that sells pies baked with charcoal.

Book a pizza tour in Chicago

30. Enter the world of Chicago crime

people in a store| ©Daniel Rangel
people in a store| ©Daniel Rangel

Hear the stories of Al Capone and The Untouchables, as well as the Chicago mob. There are many crimes committed by Chicago mobsters and you will investigate them with a professional guide and chauffeur. In other words, you will have live commentary on the bus.

Likewise, you can take pictures from the bus to various crime scenes, which makes the activity much more complete. And, as if that were not enough, you will enjoy a controlled temperature according to the weather of the moment.

Book a Chicago Crime Tour

31. Attend a fun Shakespeare play with a professional drunk actor

group of people having drinks| ©joe valenzuela
group of people having drinks| ©joe valenzuela

Have you ever seen a drunken actor doing a Shakespeare play? Well, you've come to the ideal activity; in it a professional artist with 5 shots of Whisky tries to act in a high level theatrical play. Yes, a drunken actor, as you read it, how fun it sounds.

The play takes place at "The Lounge" in The Loop district. On site you can drink craft cocktails, so the activity is limited to people 21 and older. Don't forget to book the performance via the button below.

32. Go to a Chicago Bulls game

kid in a red jersey| ©slevy15
kid in a red jersey| ©slevy15

Chicago Bulls is one of the best basketball teams in the NBA and plays various games in their hometown. In this regard, you can't miss a basketball game. Normally, basketball games in Chicago are held in the imposing multi-sport pavilion United Center.

Moreover, at the United Center in Chicago you can watch different NBA teams, so don't miss this opportunity. Best of all, throughout the year you can buy tickets to a Chicago Bulls game, so plan your visit to the Windy City well.

33. Explore the Museum of Contemporary Art, Chicago

Man sitting and looking at art| ©Mary Warren
Man sitting and looking at art| ©Mary Warren

At this museum you can view contemporary art galleries any time of the year. Admire the architecture of this expansive museum, which opened in 1967. Inside the museum, various events are held for the general public. However, you must pay to attend some of them.

Note that you can observe various works by artists who are still alive, that is, artists of our time. Likewise, the museum has a store, restaurant and bar, so you can spend a different time eating among incredible art galleries or simply buy some souvenirs.

34. Take a street art tour in Chicago

Street Art| ©Daniel Lobo
Street Art| ©Daniel Lobo

While many overlook Chicago's street art, this walking tour will take you to the most artistic and iconic streets of the city. Murals, small graffiti and contemporary street artwork will leave you open-mouthed, thanks to their colorful designs.

The technique of street artists can be seen in streets like The 606 or in Wicker Park, ideal places for lovers of murals and graffiti. If you want to go to the bathroom or eat and drink something delicious, don't worry, because you will enjoy a stop at the Ipsento coffee shop.

Book a Chicago street art tour

35. Play and escape through a 60-minute experience in Chicago

River North| ©Mitchell Joyce
River North| ©Mitchell Joyce

At River North you can enjoy a 60-minute escape game. There are several options to choose from, for example, the "Gold Rush" game, through which you must find gold to achieve victory. There is also a game called "Special Operations", for you to become a secret agent and solve a complex case.

Another game that this tour offers is "Prison Break", in which you'll have to escape from prison as best you can. As if that were not enough, you have other options such as "The Heist", a game in which you must recover a stolen work of art.

Book an escape room in Chicago

36. Delight your palate in the best places in Chinatown.

entrance to the Chinese restaurant| ©edwardhblake
entrance to the Chinese restaurant| ©edwardhblake

Undoubtedly, one of the neighborhoods where you can find excellent cuisine in Chicago is Chinatown. This Chinatown is one of the 9 Chinatowns in the United States. The Asian style houses and stores will surprise you a lot, so take a good camera to take pictures.

Of course, the Asian cuisine ranges from Chinese street-style fried rice to chop suey. Other dishes you can see on this tour are Cantonese dim sum, Sichuan chicken and Mongolian stews. Note that the food tour will take you to different restaurants in Chinatown such as Lao Sze Chuan.

37. Walk through the Medieval Torture Museum

museum information sign| ©Doss
museum information sign| ©Doss

In this museum you can see different tools of torture, macabre interrogations and immobilization of people. In addition, there are different waxen assassins with their bloody victims showing the atrocious tortures that existed at some point in history.

Also, you will enjoy clear and informative audio about each torture device. This site has a size of 6000 feet, so you will be able to see different aspects related to the tortures of the medieval times.

Book tickets for the Medieval Torture Museum

38. Eat delicious donuts around Chicago

donut with coffee| ©Thomas Hawk
donut with coffee| ©Thomas Hawk

Because there are many people like me who love donuts, I recommend the amazing Underground Donuts tour. Through this tour you'll enjoy a taste of delicious donuts at Chicago favorites like Dappeer Doughnuts, Firecakes, Do-Rite Donuts, Stans and Doughnut Vault.

And, don't worry, as vegan and gluten-free doughnuts are also available, as well as traditional doughnuts with all the toppings. You should let the tour organizers know in advance so they can accommodate your requirements.

Book the donut tour in Chicago

39. Spend an enjoyable afternoon in the Navy Pier area

Navi Pier as seen from afar| ©Gio Mag
Navi Pier as seen from afar| ©Gio Mag

The Navy Pier area (on the shores of Lake Michigan) provides several entertainment options for an enjoyable afternoon with your family or friends. From mechanical attractions for adults and children to live music.

Also, in this place you can buy clothes and food, thanks to its various fashion stores and restaurants. In addition, Navy Pier allows you to see free dance, theater and other cultural events. There are even fireworks on occasion, so you'll have to wait for nightfall.

40. Ride a Harley-Davidson in Chicago

Harley-Davidson information sign| ©Robert John
Harley-Davidson information sign| ©Robert John

Enjoying the streets and avenues of the Windy City at your own pace on a motorcycle is like no other, especially for Harley-Davidson, BMW and Indian Pursuit enthusiasts. The good news is that you don't have to buy these types of motorcycles, you just have to rent them.

At Rental Motor Bike you can choose the bike you like the most. By the way, another of my favorite motorcycle models to ride around Chicago is the Honda Goldwing 1800, of course, apart from models like Harley-Davidson Pan America 1250. Do you dare to ride a motorcycle around Chicago?

41. Distract your eyes with Michelangelo's works in Chicago

white structure| ©Oleksandr Pidvalnyi
white structure| ©Oleksandr Pidvalnyi

Chicago's Sintine Chapel Exhibit is home to an immersive Michelangelo photo gallery. This painter's works left a huge mark on the Vatican, and now you can get a close-up look at high-resolution images of his epic paintings.

The people in charge of this site have done Star Trek and Titanic exhibits, so you can imagine the high quality of this activity. In fact, they have done exhibits of Michael Jackson and Frida Kahlo. If you like painting, be sure to visit these types of exhibits in Chicago.

42. Feed a giraffe at Brookfield Zoo

zoo information sign| ©Paula Longshore
zoo information sign| ©Paula Longshore

In addition to feeding a giraffe you can enjoy other animals such as dolphins, butterflies, birds and much more. At Brookfield Zoo there are no limits, as there is even a carousel for the whole family to enjoy. There is also the Hamill Family Play Zoo, ideal for adults and children.

In fact, if you want, you can adopt an animal from the zoo and help take care of it, just go to their official website to learn more about it. And, of course, one of the favorite attractions of this zoo is that you can feed a giraffe, yes, now your dream is possible.

43. Kayak the Chicago River

people kayaking on the Chicago River| ©Brian Kay
people kayaking on the Chicago River| ©Brian Kay

In a high quality kayak you can freely navigate the Chicago River. Stop for a moment if you want to admire the great architectural works of the city from the water. For example, Art Deco buildings and modern architecture, including incredible skyscrapers.

You can rent a kayak in Chicago to enjoy nature and urban views at the same time. The kayak and safety accessories are included for this activity.

44. Tune your senses with classical music by candlelight

young people playing instruments on stage| ©Sun Valley Group of Schools
young people playing instruments on stage| ©Sun Valley Group of Schools

With the Candlelight Concerts experience you will hear everything from classical music to tributes from Beyoncé, Queen or Adele. All in a unique candlelit atmosphere that will relax your mind and sharpen your senses.

Some events at the venue have been tributes to Aretha Franklin, Juan Gabriel and Taylor Swift, so there is music for different tastes. I even recommend the concerts inspired by anime music, as they offer a mix of feelings for anime fans.

45. Get creative with your kids at LEGOLAND Discovery Center

entrance to Legoland| ©swimfinfan
entrance to Legoland| ©swimfinfan

Unleash your ideas at the LEGOLAND Discovery Center in Chicago. There you will find millions of LEGO bricks and various masterpieces, for example, iconic city buildings in LEGO version.

In Kingdom Quest you can destroy skeletons and in the movie theater you can see your favorite LEGO characters. Without a doubt, this is a highly recommended activity for the whole family, as you surely love the LEGO world as much as your children do.

46. Visit Frank Lloyd Wright's Home and Studio

people outside at Frank Lloyd Wright's Studio| ©Joseph Hollick
people outside at Frank Lloyd Wright's Studio| ©Joseph Hollick

Learn about architecture at the home of the famous Frank Lloyd Wright. Inside you can observe the architectural works that Wright completed. Note that the Prairie style was created in this studio, and you will even see the first work of this incredible architectural style.

What are you waiting for? Book a guided tour of Lloyd Wright's Home and Studio, which includes a tour of the surrounding area. Architecture lovers and students can immerse themselves in the world of Frank Lloyd Wright with this guided tour.

47. Experience a skydiving simulation in Chicago.

Two skydivers flying in the wind tunnel.| ©Joseba Zubiaurre
Two skydivers flying in the wind tunnel.| ©Joseba Zubiaurre

Are you a little scared of jumping out of an airplane? Don't worry, with this experience you can experience skydiving indoors, as there are several skydiving entertainment centers in Chicago. This is a safe air tunnel system with an expert guide, who will explain how to position your body when falling from an airplane (before releasing the parachute).

Keep in mind that this activity can also be done by your children, so everyone will enjoy it as a family. One of the companies that professionally perform this type of activity is iFLY, which is located in Lincoln Park. There are also other tourist agencies that can offer this activity; check the following link for more information.

Book a skydiving simulation experience in Chicago

48. Let your children play at the Chicago Children's Museum

child playing with blue and red pieces| ©Paul_Henry_
child playing with blue and red pieces| ©Paul_Henry_

At the Chicago Children's Museum you will find a space where play and learning merge. This activity is specially designed for children, but parents can go in with them and play with both of them. One of the attractions of the place is a tree house, without a doubt, something that children will love.

Another activity is Cloud Booster, where your kids get a workout as they go through a mesh tunnel that is quite fun and safe. Also, since most kids love the world of dinosaurs, here they can find an expedition of dinosaurs and skeletons of these amazing animals. In fact, there are dinosaurs recreated in Jurassic Park-style form, so to speak.

49. Take pictures at the Cloud Gate (The Bean)

people around the Cloud Gate| ©austin02
people around the Cloud Gate| ©austin02

In 2004 the great artist Anish Kapoor created The Bean, one of the most impressive sculptures in the city of Chicago and it's totally free. That's right, you won't have to pay to get close to see this piece in AT&T Plaza, which is part of Millennium Park. This is an activity that you can better enjoy during the day, but also some tourists like me prefer to go at night, since this way you can see the buildings or skyscrapers illuminated, being an ideal occasion to take several epic photos.

However, if you go during the day or at night you will be able to see how the Cloud Gate reflects the people of the site, thanks to its smooth and polished mirror-like surface. Don't forget to visit the surroundings and have a delicious meal with your loved ones.

This activity is included in several Chicago tours, but going on your own will allow you to take as much time as you want for photos and entertaining moments. Here is the exact address according to the Google map.

50. Get your body wet at Whealan Pool Aquatic Center

blue water park| ©curtis locke
blue water park| ©curtis locke

At the Whealan Pool Aquatic Center there is fun for the whole family. It's a large pool with slides for all ages and water rides designed for younger children.

If you don't know how to swim, this site can be the perfect place to learn, thanks to swimming lessons of up to 30 minutes, which are conducted by expert swimmers. Also, you should know that there are places to rest and even a food store. Don't you get hungry when you go to the pool? I am.

51. Visit the historic home of Frederick C. Robie

orange brick house| ©willie__
orange brick house| ©willie__

Another of Frank Lloyd Wright's creations is the imposing Robie House. This is one of the most important architectural works of the 20th century and was built between 1908 and 1910. You can enter the site Monday through Friday, but you must book in advance.

The Robie House is also Wright's last prairie-style work and is considered a historic landmark in the United States. It is also a UNESCO World Heritage Site. By the way, the work has an approximate size of 18 x 55 meters, so it is quite large. And it is worth mentioning that inside there is a wheelchair for disabled people.

52. Dance and drink with friends in Chicago's nightclubs

people dancing in a bar| ©Daniel Rangel
people dancing in a bar| ©Daniel Rangel

Chicago has several nightclubs, including some focused on the gay public. For example, there is Smart Bar, which offers drag shows, exotic dancers and a large number of themed events such as Madonna, Prince or Björk. There are also activities alluding to the 80s.

But, if you are not very interested in a nightclub for a gay audience, I recommend The Underground, which is one of the favorites of electronic music lovers. Of course, people with any sexual preference can enter this place, but all must respect an elegant dress code. And best of all, excellent DJs from all over the world have performed there, and you might even see a celebrity or two in the audience.

On the other hand, there is the Smart Bar, which focuses on dance music, so dancing and drinking there will be a very pleasant experience for lovers of this musical genre. In fact, famous DJs from various parts of the world and, of course, from the United States have played there.

53. Stop by the Superdawg Drive-In and eat in your own car

Superdawg Drive-In| ©Jim Hill
Superdawg Drive-In| ©Jim Hill

The legendary Superdawg Drive-In restaurant awaits you if you are out and about in Chicago. Here you can find mainly delicious hot dogs and hamburgers.

In addition, there you can buy drinks and side items (e.g. fries). Luckily, you can do everything from your car, which is an excellent option to avoid paying for parking. The customer service staff will treat you very well and will answer your questions when you place your order. Simply go to the ticket office with your car, you don't even have to get out to pay.

54. Learn history and see curiosities at the Chicago History Museum

history museum sign| ©Alan Partridge
history museum sign| ©Alan Partridge

At the Chicago History Museum, there are collections from a variety of designers who made fashion history. For example, Stephen Burrows, Patrick Kelly and Scotty Piper. However, you should check their website to find out which galleries or collections are available at the time of your visit.

Likewise, in this place you will learn about historical aspects of Chicago and, if you want, you can hire a local and expert guide to learn about the city from a historical point of view. Usually, on the occasion of Halloween there are some haunted events that will amuse the whole family. In fact, in December, there are some very exciting Christmas activities, so there is high quality entertainment all year round.

55. Learn about aspects of Latino culture at the National Museum of Mexican Art

National Museum of Mexican Art| ©BORIS G
National Museum of Mexican Art| ©BORIS G

Latino art comes to Chicago through the National Museum of Mexican Art. There are various activities throughout the year, such as the Day of the Dead event. The museum also offers workshops, book readings and art festivals on various dates.

In the same vein, there is a permanent collection of Mexican history and aspects of the border with the United States. In this collection you will see Mesoamerican objects, popular art and modern Mexican art. Relax and immerse yourself in Mexican culture and its evolution throughout history.

56. Speed up on Lake Michigan

person on a jet ski| ©fjsmalaga
person on a jet ski| ©fjsmalaga

Want to ride a Yamaha VX110 jet ski on Lake Michigan? Well, this activity is waiting for you, as it offers motorcycles in excellent condition and essential accessories such as life jackets and safety belts. This way, you will be able to admire the Windy City from the water.

Note that you can rent a jet ski from Jet Ski, and it is even possible to take lessons with a professional from the company before sailing on your own. By the way, the jet skis have 110 horsepower, so you'll be going at a speed that won't bore you for a second.

57. Get up close to the animals at Lincoln Park Zoo

Zoo entrance| ©Jack
Zoo entrance| ©Jack

At Lincoln Park Zoo you can see various wild and exotic animals from a safe distance. Among the animals are rhinoceros, red panda, hippopotamus and Japanese macaque. Also, other animals such as the Jamaican iguana or the African penguin.

In total, there are approximately 200 different species of animals, so it will be a nice experience to go as a couple or with the whole family. Likewise, you will find gardens with more than 1200 species, for example, the American elm and wild apple trees, which are very beautiful.

58. Listen to great music at the Chicago Jazz Festival

jazz band on stage| ©robert.fr.22
jazz band on stage| ©robert.fr.22

Every year the Chicago Jazz Festival is held, featuring local, national and international artists. This is an activity that usually takes place annually around Labor Day. In addition, the festival lasts between 8 and 9 days.

The jazz concerts are held at different venues in the city and tickets are free. Some of the venues where there are usually live performances are The South Side Jazz Coalition, Constellation, Sleeping Village, Hungry Brain, Live the Spirit Residency and The Birdhouse Inc. However, check the full schedule before you travel.

59. Get inebriated at Chicago's rooftop bars

glass of wine and glasses on the table| ©Timur Saglambilek
glass of wine and glasses on the table| ©Timur Saglambilek

Cocktails and other drinks await you at Chicago's fabulous rooftop bars. I start by talking about Z Bar, but not because it is the best or the worst, because I really like the three options I recommend here. The Z Bar is very striking at first glance, so for photos or selfies of the city it is a spectacular place. There you have high quality food and drinks.

Another rooftop bar you should definitely check out is the Cerise Rooftop, which offers live music with excellent local DJs and is also close to your room if you decide to stay at the Virgin Hotels in Chicago.

Finally, I recommend Tony's Rooftops Bar, where you can have a delicious meal with wine and high-quality cocktails. Interestingly, this bar is named after Time Out founder Tony Elliott and features vintage Time Out London rooftops, as well as elegant wooden beams and twinkling lights that decorate the place nicely.

60. Enter Ernest Hemingway's Birthplace Museum

beige and green building| ©Irina Hynes
beige and green building| ©Irina Hynes

The Ernest Hemingway Birthplace Museum is located in Oak Park, west of Chicago. Ernest Hemingway was born on the second floor of this house and is one of the leading writers and novelists of the 20th century. The architecture of the house is in the Queen Anne style, so it is a popular site for tourists and students because of its architectural significance.

The house was built in 1890 and was the first to have electricity in Oak Park. If you enter the museum, you can admire both the interior design of the period and the antique furniture. And, of course, in this house you'll hear stories of this amazing American writer, who lived there in his youth.

61. Explore the DuSable Museum of African American History

Museum Information Sign| ©Smart Chicago Collaborative
Museum Information Sign| ©Smart Chicago Collaborative

The DuSable Museum of African American History honors African American figures who left their mark on the country. You'll also see stories about Africans who came to the United States during the slavery era.

Likewise, there you will find antique furniture that was and still is important to the history of African-American culture. And among its collections is a Charles C. Dawson watercolor painting. You'll even find a George Washington Carver painting in a laboratory.

62. Experience a sunset boat ride

yellow boat on the lake| ©Aaron Burden
yellow boat on the lake| ©Aaron Burden

Enjoy a romantic experience watching the sunset and the beautiful Chicago skyline from Lake Michigan. There are several boat tours available, so you can also choose from a variety of boats (sailboat, cruise ship, speedboat, etc.). Without a doubt, this is a special activity that you should experience with your partner. If you add to this a glass of wine or a delicious appetizer, it will be much more interesting.

In this same sense, there are boats that include a ride to see the fireworks in the Navy Pier area. Even if you know how to sail or want a private sailboat, you can rent one; in Chicago almost anything is possible. Here you can check out the different sunset boat tours. This type of activity will leave a nice memory for couples about their visit to Chicago.

63. Ice skating at Maggie Daley Park

aerial view of ice skating rink| ©Brian Kay
aerial view of ice skating rink| ©Brian Kay

Maggie Daley Park has an ice skating rink that is usually open in the winter. It is a large rink with side safety bars. You can skate there for free if you bring your own skates. However, to enjoy free skating you should check the schedules on the website, as at some times of the day free skating is not allowed.

Also, you can pay for skate rentals in case you don't have them, so yes or yes you can have an ice skating experience at Maggie Daley Park. And another important thing you should know about this activity is that the park has other attractions for the whole family, and there is even a food stand on site.

64. Eat a delicious ice cream at Rainbow Cone

girl eating ice cream| ©Parker Johnson
girl eating ice cream| ©Parker Johnson

There is an excellent locally sourced ice cream parlor in Chicago and that is Rainbow Cone. If you love ice cream, you must visit to try their unique and delicious flavors. One of my favorite ice cream is the Original Rainbow Cone, which has 5 flavors, Chocolate, Orange Sherbet, Palmer House, Pistachio, Strawberry. In other words, this ice cream is the main specialty of the house.

In addition, in this local ice cream parlor you can enjoy mini donuts with coffee, a recent addition to its extensive menu. Another exquisite appetizer is the chocolate cake with the 5 rainbow flavors. Undoubtedly, you will feel like a kid eating candy at this ice cream parlor. By the way, you can go to Rainbow Cone with the whole family without any problem.

65. Listen to blues bands at Buddy Guy's Legends

man playing saxophone| ©Kris Long
man playing saxophone| ©Kris Long

Listening to live blues is one of the top activities for locals and visitors to Chicago. You should know that blues and jazz are two musical genres that are part of the city's culture. For this reason, at Buddy Guy's Legends there are many national and international blues and jazz concerts.

And, as it could not be missing in a blues bar, there is food from New Orleans, the city where blues is historically believed to have been born. This place is run by Buddy Guy, a blues legend who, if you are a fan of the genre, surely you have heard his music.

On the other hand, you should know that the musicians who play in this bar are quite talented, for example, Ivy Ford, Paul Nelson, Joana Connor and Demetria Taylor, just to name a few. Also, there are top blues bands such as Liz Mandeville & Big Dez and The Nu Blu Band.

66. Cheers for the Chicago Blackhawks field hockey team

view from the crowd of the field hockey arena| ©pmonaghan
view from the crowd of the field hockey arena| ©pmonaghan

Chicago Blackhawks games are held at the United Center. This team is very important for locals and visitors who want to see in person a field hockey game in a real rink and with professional NHL players.

The official website offers group tickets, individual tickets and season offers; don't forget to check the upcoming Chicago Blackhawks games before traveling. Also, be advised that tickets are available for seniors and VIP members. Either way, go and cheer on the team at one of their games, which are held at various times throughout the year.

67. Take advantage of the free Millennium Park Summer Music Series concerts

band on stage| ©Pete
band on stage| ©Pete

Music is an intrinsic part of Millennium Park, and if you want to enjoy free concerts, you can attend the Summer Music Series. These take place during the months of June, July and August, but only on Mondays and Thursdays. Don't miss the musical activities if you go to Chicago during these months of the year.

Well-known and emerging artists perform at the Jay Pritzker Pavilion, which is easily accessible from Randolph Street, Millennium Garage or Monroe Street. In addition, activities are usually held from 6:30 pm to 9:00 pm.

Some of the artists that have performed there are Abigail Washburn, Gabriel Garzón Montano, Brandi Clark, Samantha Crain, Chicago Immigrant Orchestra, Jeff Tweedy, Escuela Popular de Música and Ana Tijoux. Here you can find information about the Millennium Park Summer Music Series.

68. Be amazed by the different acrobatics of the Chicago Air & Water Show

group of airplanes doing aerobatics| ©didimouman
group of airplanes doing aerobatics| ©didimouman

This free event is put on by the city of Chicago and features a series of planes and expert pilots performing aerobatics over Lake Michigan and North Ave Beach. Also, you should know that this is the largest aerobatics activity in the United States.

How much does it cost? Don't worry about the price, as the activity is totally free and you can watch it from any point on the shore of Lake Michigan. When does it take place? Generally, it takes place in the summer (August), to better see the acrobatics in clear skies. Bring your umbrella to protect you from the sun, as the show lasts 4 hours.

For more information visit the Chicago Air & Water Show website.

69. Admire the plants at the Garfield Park Conservatory

Garfield Park Conservatory| ©Steve Kuenstler
Garfield Park Conservatory| ©Steve Kuenstler

Its 8 gardens behind glass will leave you open-mouthed, as they have thousands of plants from various parts of the world. The most impressive thing is that the plants are behind glass, so that they are better preserved. This is known as landscape art under glass.

In addition, in this botanical conservatory there are several natural environments for children and a water lily pond. Also, this site has 10 acres of open gardens for the whole family. If you are inside the conservatory, you will experience tropical temperatures, which is an added bonus for any visitor.

Here is more information about the Garfield Park Conservatory.

70. Laugh at the many faces of the Crown Fountain

Crown Fountain| ©Igor Sorokin
Crown Fountain| ©Igor Sorokin

Going to the Crown Fountain in Millennium Park will allow you to enjoy incredible urban views and at the same time laugh at the funny faces in the video sculpture. This fountain was designed by Spanish artist Jaume Plensa and built by Krueck and Sexton Architects. Note that the work was inaugurated in July 2004.

On the other hand, I inform you that the work has two towers or video sculptures at each end and on the ground a sheet of water. You can walk around the entire work, wet your feet and admire up close the faces of people opening their mouths. By the way, this is the address of the Crown Fountain according to Google Maps. You don't have to pay to see the fountain, as it is public.

71. See the Buckingham Fountain at night

Buckingham Fountain at night| ©Snejana Iordanova
Buckingham Fountain at night| ©Snejana Iordanova

This incredible urban water fountain is located in Grant Park and is one of Chicago's most treasured landmarks. It was designed by British-American artist Edward H. Bennett. Likewise, I tell you that the monument is inspired by the Latona Fountain.

It is worth mentioning that in this work you can see small statues in the shape of horses where the water comes out. By the way, although you can admire the imposing work during the day, I also recommend you do it at night, as it has a very colorful and striking light show. Don't wait any longer to go see it and take a few pictures in front of it.

Check the address of Buckingham Fountain and plan a visit. Luckily, it's a public fountain, so there's no entrance fee or tax to pay.

72. Marvel at a Broadway Show in Chicago

James M. Nederlander Theatre| ©League of Historic American Theatres
James M. Nederlander Theatre| ©League of Historic American Theatres

The James M. Nederlander Theatre is the official home of several Broadway shows in Chicago. This theater was opened in May 1926 and boasts an architectural style of the era.

The first "Broadway in Chicago" play to be performed in this theater was Wicked, for 3 long years. As of 2019 it was named after Broadway founder James M. Nederlander. Today it is still home to Broadway shows in the Windy City, so you can check out their page to properly schedule a visit to the theater.

Some of the events that have been performed there include "The Lion King," "Les Miserables" and "Disney's Aladdin." Do you like Broadway plays and musicals? In Chicago you can also see some shows.

73. Sing and scream at the Lollapalooza Festival

people gathered on the concert field| © Danny Howe
people gathered on the concert field| © Danny Howe

If you like various music festivals, I recommend Lollapalooza, which takes place every July in Chicago. The most popular music genres at this festival are rock, punk rock, metal and electronica. You should check the official Lollapalooza website for information about the next edition.

Internationally renowned artists and bands such as Metallica, Dua Lipa and Green Day have performed at this festival. By the way, Lollapalooza takes place in Grand Park, so you have several lodging options nearby. Keep an eye out for ticket sales so you don't miss out, as tickets are hard to come by closer to the festival date.

74. Tour the Museum of Science and Industry

museum entrance| ©Paul_Henry_
museum entrance| ©Paul_Henry_

The Museum of Science and Industry offers endless scientific experiments and incredible exhibits for you to learn more about the scientific and industrial world. Also, you should know that this museum has 400,000 square feet of exhibit space.

One of the attractions in this museum is a 5-story screen for the cinematic world. And, of course, my favorite attraction is the German U-505 submarine from WWII. This submarine makes your hair stand on end with its excellent design and the history that brought it to the United States. Interestingly, the U-505 is the only German submarine in the country.

75. Be in awe at the Lyric Opera of Chicago

view of the stage from the back seats| ©Timothy Neesam
view of the stage from the back seats| ©Timothy Neesam

Chicago boasts excellent classical and contemporary operas, thanks to the Lyric Opera of Chicago theater, which features national and international opera artists and orchestra. In addition, you can enjoy not only various opera events, but also musicals and other cultural activities.

This theater is very well designed acoustically for high-level musical performances, so no matter where you sit in the hall, you will always clearly hear the music being played on stage. By the way, at the Lyric Opera of Chicago there is not only live music, but also educational and innovative activities.

76. Experience delicious, unforgettable dishes at Alinea

people tasting food at the restaurant| ©Steve Jurvetson
people tasting food at the restaurant| ©Steve Jurvetson

Alinea Restaurant is one of the top 3 Michelin Star dining venues in the United States. So, if unique food prepared by national and international chefs is your thing, this is the ideal choice. Eating here is an unforgettable experience if you like modern flavors.

In addition, this restaurant has received several awards such as Best Restaurant in the U.S. according to Gourmet and Business Insider and "Best Restaurant in the World" by Elite Traveler. Undoubtedly, the dishes you will taste here are a work of culinary art. On their official website you can make a reservation, don't wait any longer to eat at Alinea Restaurant!

77. Give your children a unique play experience at Pirates' Cove theme park

pirate ship at night| ©Jared Beaney
pirate ship at night| ©Jared Beaney

Kids will have the time of their lives on the various attractions at Pirates' Cove Children's Theme Park. Among the attractions is an 18th century pirate ship, where your children can let their imagination and creativity run wild.

On the top floor of the pirate ship you will find a room for birthday parties. There is also a place called Cannonball Falls for picnics. In fact, this area is so large that it can accommodate 5 birthday parties at a time. However, Cannonball Falls is available for full reservation on Thursdays, Saturdays and Sundays from 5:00 pm to 8:00 pm.

78. Fill your stomach at the Taste of Chicago food festival

person buying pizza| ©jorjeanna
person buying pizza| ©jorjeanna

If you go to Chicago in June or July, you can't miss the Taste of Chicago food festival. This festival takes place in different places in Chicago such as Grant Park, so check out all the information on the website above.

This is the perfect activity to fill your stomach with the best local restaurants. This festival only takes place on Saturdays, which you should be aware of before your visit to Chicago. Also, don't worry about parking your vehicle, as there are several options such as Grant Park North Garage, Millennium Park Garage or Grant Park South Garage.

79. Enjoy a family experience at the Peggy Notebaert Nature Museum

Green bird on a branch| ©tieulinhclc - Thanks for 2 million + views
Green bird on a branch| ©tieulinhclc - Thanks for 2 million + views

As part of the Chicago Academy of Sciences I recommend the Peggy Notebaert Nature Museum. This place is a plus for the whole family's workout, as it has children's attractions and butterfly gardens for people of different ages.

This museum is open every day and also offers views of animals such as rodents and frogs. The museum also offers creative art classes, Critter Connections and outdoor explorations. Take your kids to this museum where they can learn while having fun.

For more information about the museum, visit their official website.

80. Walk inside Bloomingdale's and shop for various products.

Entrance to Bloomingdale's| ©Ryan
Entrance to Bloomingdale's| ©Ryan

At Bloomingdale's in Chicago you can find different departments such as jewelry and home goods. In addition, each department store offers unique products that are only available on site or are sold there for the first time. Likewise, at Bloomingdale's there are different beauty and personal care services.

On the other hand, while spending time there looking at their products you can stop for a bit and grab a bite to eat or drink at Forty Carrots. Here you can eat delicious yogurt ice cream, smoothies and other snacks such as salads or sandwiches. In addition, inside Bloomingdale's there are plenty of clothing stores, such as Lafayette 148, David Yurman, Chloé and Canali 1934.

81. Learn at the Richard H. Driehaus Museum

Candelabra lit| ©Stephanie Barto
Candelabra lit| ©Stephanie Barto

The Richard H. Driehaus Museum features several historical attractions such as the Great Chicago Fire of 1871 or the incredible Tiffany stained glass windows, also known as The Tiffany Trail. Another interesting experience can be found in the Nickerson Mansion.

Also, you should know that the museum offers an app for iOS and Android, which allows for self-guided tours on all 3 floors. It is recommended to go to the museum in person for a more immersive experience at the site. Your mobile device must have internet data, as you won't have free WiFi network there.

Other things I should warn you about are to download the app before going to the museum and bring a headset or headphones with you. This is because the app offers excellent audio that will guide you through the museum.

82. Appreciate jazz in all its splendor at The Green Mill

band playing| ©rebecca anne
band playing| ©rebecca anne

Enjoy an authentic jazz experience at The Green Mill, a bar that offers the best local jazz bands and artists, but also foreign artists on various special occasions. The venue hosts performances every day, so if you're in Chicago, you're sure to be able to have a drink while listening to great music at the bar.

The Green Mill also offers comedy and poetry events for those who don't listen to jazz to enjoy. By the way, the sound of the place is wonderful, everyone can enjoy complex harmonies and syncopated drum rhythms with high clarity.

83. Get a relaxing massage at a Chicago spa

woman getting a facial| ©Raphael Lovaski
woman getting a facial| ©Raphael Lovaski

As you might guess, there are many luxurious, refreshing and relaxing spas in Chicago, so before you head home you should stop by one of them. For example, The Peninsula Spa is one of my favorites. There you will be attended by people specialized in skin treatments and massages. Not for nothing is it known as Chicago's urban oasis.

Relax your mind, body and spirit like never before in this wonderful luxury spa where you will find yourself enveloped in Asian and Ayurvedic philosophy. Some of the experiences offered at the spa are natural stone massages, aromatic oils or the popular Marma massage.

Other spas I recommend you visit are Allyu Spa, Spa Space Chicago and Chuan Spa at The Langham.

84. Cheer on the NFL's Chicago Bears at an NFL game

playing field from on high| ©drummergrrl
playing field from on high| ©drummergrrl

Another must-see Chicago activity is a Chicago Bears game. This American soccer team usually plays in its home city, especially, at the Soldier Field multi-purpose stadium. The games are held on various dates each year, so you should visit the official Chicago Bears website to keep up to date and buy tickets in advance.

This monumental soccer stadium has also been home to many concerts of famous national and international artists. One of the most striking things for locals and visitors alike is the ample size of Soldier Field and the adrenaline rush you feel when cheering for your favorite team with thousands of people around you.

85. Arrive early and have a delicious meal at Au Cheval

chef preparing hamburger| ©Spanish Hipster
chef preparing hamburger| ©Spanish Hipster

Looking for a restaurant where you don't have to make reservations to visit? You have come to the right activity, the Au Cheval Restaurant does not require reservations, but the entrance is on a first come, first served basis. There you can eat hamburgers with steak and smoked bacon.

Likewise, at Au Cheval you must try the Bologna, which is one of the main ingredients in their recipes. And not only will you be able to eat the delicious in this restaurant, but there are also drinks of all kinds, so that the experimentation will be much more enjoyable. Don't forget to arrive early to avoid queues.

86. Head to Dusty Groove to buy vinyl

Vinyl in order| ©Patrick Foisy
Vinyl in order| ©Patrick Foisy

This place is like paradise for CD and vinyl collectors, as here you find original albums from various retro bands and artists, as well as from today's world. Rock, funk, Soul and hip hop are just some of the music genres in their stock. There are thousands of vinyls from all over the world, including rare or little known albums.

You can view the vinyl catalog on Dusty Groove's official website, and it is even possible to buy online, as the company ships nationally and internationally. There are constantly new vinyls in their library, maybe you'll find here the vinyl you've been looking for everywhere.

87. Try different specialty foods at Time Out Market.

people sitting at the tables| ©Harry Carmichael
people sitting at the tables| ©Harry Carmichael

Sample food from various regions of the world or various well-known brands here at Chicago's Time Out Market. Also, the site has a 50,000-square-foot hall where you will not only eat, but also enjoy live music. There are also other activities for children and even yoga.

Likewise, this place offers excellent services for work groups, birthdays or semi-private meetings with your friends. Of course, I can't end this review without mentioning some of the culinary options at Chicago's Time Out Market: fried chicken, hamburgers, hot dogs, desserts, salads and more.

88. Surprise yourself with a concert by the Chicago Symphony Orchestra

group of people playing violin| ©Samuel Sianipar
group of people playing violin| ©Samuel Sianipar

Do you like classical music? Then you can't miss a concert of the Chicago Symphony Orchestra, which has been active since 1891 and is one of the most important in the world. Also, you should know that the orchestra's conductor Riccardo Muti is giving his last season after 13 years of hard work.

Also, to enjoy the best concerts you have several subscription options such as CSO Classical Thursday I, CSO Classical Saturday B, CSO Classical Saturday E, CSO Classical Saturday G, CSO Classical Saturday H, CSO Classical Sunday A and CSO Classical Tuesday B.

Among the works featured are Prokofiev's Sixth, Rachmaninov's Symphony No. 2, Shostakovich's Eighth, Beethoven's Missa solemnis, Mozart's Symphony No. 40, among others. This does not mean that the works are repeated, as they vary. In other words, the orchestra presents new works throughout the year.

Run and buy your ticket for the Chicago Symphony Orchestra and live a different experience that disconnects you from your daily routine.

89. Learn about archaeological discoveries at the Oriental Institute of Chicago

person viewing oriental art| ©Daniel & Kate
person viewing oriental art| ©Daniel & Kate

Another activity you should not miss is a visit to the Oriental Institute of Chicago. There you can see various archaeological discoveries such as tablets, photographs, The Court of Yelda Khorsabad, The Mesopotamian Gallery of Edgar and Deborah Jannotta, The Syro-Anatolian Gallery Henrietta Herbolsheimer MD, The Persian Gallery of Robert and Deborah Aliber, The Nubian Gallery of the Robert F. Picken family, The Egyptian Gallery of Joseph and Mary Grimshaw, etc.

For example, in Joseph's gallery you will see 800 objects from the Predynastic period to the Byzantine period, a 17-foot tall statue of King Tutankhamun you will see at the entrance of the gallery. Likewise, in the court of Yelda Khorsabad the most incredible objects you'll see is the 16-foot tall Human and the Winged Bull of the Head.

90. Cheer for the Chicago Fire team at Soldier Field

Soldier Field entrance| ©Jason Pryor
Soldier Field entrance| ©Jason Pryor

Who doesn't love soccer? If you are a fan of the team then cheer on the Chicago Fire at Soldier Field, the multi-purpose stadium that has a capacity of 61,500 spectators. As a curious fact you should know that it was built as a tribute to the people who died in the First World War.

Undoubtedly, it will be an unforgettable experience to be in this stadium with the locals and support their team. To buy tickets to the games here I leave you the official website of the Chicago Fire Football Club.

91. Ride the roller coasters at Six Flags Great America

Red attraction| ©Jeremy Thompson
Red attraction| ©Jeremy Thompson

Feel like a kid enjoying the attractions of Six Flags Great America, especially, enjoy its 15 roller co asters and let out all the adrenaline inside you. In addition, you can live this experience in the company of your family, since in this site there are also 3 children's themed areas, spectacular shows and an incredible water park with 20 acres.

There are also other activities that you can enjoy such as festivals and music concerts, so it is worth visiting this amusement park in Chicago. However, some of these events are available in specific months, so here is more information about Six Flags Chicago.

92. Have a drink at the Hard Rock Café in Chicago

Hard Rock Cafe| ©Philippe Reichert
Hard Rock Cafe| ©Philippe Reichert

This iconic place is located in the River North neighborhood. Not only will you be able to have a few drinks there, but you will also see amazing pieces of music legends like Jimi Hendrix, Billy Joel, Prince and Buddy Guy on the walls.

Also, you have different gastronomic options like burgers, bruschettas, wings, classic nachos, sandwiches, salads, ribs, fajitas, hot fudge brownie, ice cream, cheesecake, as well as a menu for kids.

If you are interested in this place, I recommend buying a ticket to the Hard Rock Café Chicago online before traveling, as you must be sure of its availability before getting on the plane.

93. Tan your body at Oak Street Beach

aerial view of the beach| ©Jonathan J. Castellon
aerial view of the beach| ©Jonathan J. Castellon

On the shores of Lake Michigan is a favorite beach for locals and tourists of all ages. This is Oak Street Beach, where you can tan your body and swim. However, you should make sure that the beach is open on the day of your visit to Chicago, as due to weather changes, maintenance and other reasons, sometimes the beach is not open.

How attractive is this beach? Well, the beach itself is small, but it has spectacular views of the Chicago skyline, Lake Michigan and different incredible buildings or skyscrapers. Also, from the site you can see impressive sports boats, cruise ships and sailboats in motion. If you want an unforgettable photo for your social media, come to this beach and take a wonderful selfie.

Here is the address of Oak Street Beach on Google Maps. Note that the entrance to this beach is free, but, unfortunately, it's not very easy to get parking nearby.

94. Explore Chicago Park District Golf

two guys playing golf| ©Kaleidoscope
two guys playing golf| ©Kaleidoscope

Golf in Chicago? Of course you can, this city is home to the Chicago Park District Golf, which is made up of a number of golf parks. There are even options to learn golf. The learning site I recommend is Diversey Practice Center.

Another park in the district that you should know is Jackson Park, which has 18 holes and a very striking course at first sight, thanks to its mature trees that invite you to be more precise in every shot. I also recommend Sydney R. Marovitz Park, which has beautiful views of Lake Michigan and the city's skyscrapers.

Either way, go to the golf course of your choice, as the district has a great variety, for example, I had not mentioned the South Shore Golf Course or the Robert A. Black Golf Course.

95. Feed your mind at the Smart Museum of Art

people at the smart museum| ©uchicagoalumniweekend
people at the smart museum| ©uchicagoalumniweekend

This museum is run by the University of Chicago, thus inspiring the study of art and its conservation. Its collection is quite extensive, as it has an average of 16,000 objects to admire. Also, you should know that it has worksfrom all over the world.

Another aspect that will impress you about the Smart Museum of Art is its collection of landscape and environmental paintings. Visit the museum during some of its events or exhibitions, but first go to its website to learn about its activities in detail.

96. Gambling at the Horseshoe Hammond Casino

Horseshoe Casino| ©David Beasley
Horseshoe Casino| ©David Beasley

Gambling and gambling are attractive to people from all over the world, so if you are in Chicago, you must visit the Horseshoe Hammond Casino. This casino is located next to Lake Michigan, in Casino Center Dr Hammond.

This casino is part of Caesars Entertainment, one of the best casino companies in the United States. In addition, inside there are several options such as table games and slots. Also, you can enjoy a restaurant for you to eat or drink if you wish.

97. Walk through the Pullman National Monument

Entrance to Pullman National Monument| ©Matthew Dillon
Entrance to Pullman National Monument| ©Matthew Dillon

The Pullman National Monument is a large historical site where you can find the Administration-Clock Tower Building, which has an architecture from 1880, the year it was built.

In addition, at the monument you will see the Pullman Exhibit Hall, which offers an introductory film, informative exhibits and artifacts. In addition, you should visit the National A. Phlip Randolph Pullman Porter Museum, where you'll enjoy permanent and multimedia exhibits.

98. Stop by Chicago's Skateboard Parks

kid skateboarding in the air| ©Giovanna Gomes
kid skateboarding in the air| ©Giovanna Gomes

Although the interest in skateboarding is not common in many people, in Chicago it is a little more seen. The city has excellent parks where both amateurs and professionals practice this sport. One of the parks is the Audubon Skate Park, which has an indoor and an outdoor area, and is next to a field where young people can train baseball.

Another place you should visit is the Skate Park on Sacramento Ave If you do skateboarding, practice there, because you have different rails, stairs and platforms to perform acrobatics. Also, I recommend spending some time at the Wilson Skate Park, one of the most visited skate parks by local athletes. Here you can see several people doing acrobatics on their skateboards.

Likewise, I can't leave out Fargo Skateboarding, a skateboarding store with a rink and skating lessons. This store is located approximately 2 hours from downtown Chicago (outside the city).

99. Paddleboarding (SUP) in Chicago

man paddleboarding| ©JGiacomino
man paddleboarding| ©JGiacomino

If you want to SUP (stand-up paddle) in calm waters, rent a board from Chicago Water Sport Rentals. Rentals include a life jacket, paddleboard and paddle, so you won't have to get these accessories separately.

Normally, SUP practices take place on calm Lake Michigan, a perfect place to learn this water sport. Besides, I tell you that the boards and paddle are of great quality, for example, the paddle is made of polycarbonate F2. Of course, this activity gives you the opportunity to admire the city of Chicago from the water, that is, you will have breathtaking views during your practice.

100. Dance at the Spring Awakening Music Festival

people at the night festival| ©Tamara Susa
people at the night festival| ©Tamara Susa

Among the music festivals in the United States, the Spring Awakening Music Festival stands out. Since 2008 it has brought many electronic music artists. The React Presents agency has been holding this event for several years and has brought DJs from various parts of the world.

Some of the DJs who have performed at this festival are: Armin van Buuren, Deadmau5, Martin Garrix and Steve Aoki. In other words, it is an excellent show with national and international artists of high level in the world of electronic music.

If you want to know more about this great event in Chicago (days, time, lineup and more), go to its official website.