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.
100 Fun Things to Do in Chicago

Other popular activities in Chicago

More about: 100 Fun Things to Do in Chicago

Are you traveling to the United States soon, and is Chicago one of the stops on your itinerary? Well, let me assure you that this will be one of the best experiences of your life, as this great city of more than 9 million inhabitants is one of the tourist epicenters of North America.

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

1. Take a guided tour of the city center

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

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

Most of these guided tours will take you to the most important sites in the city center, which is convenient because this is the area with the highest tourist traffic. So having an itinerary that is tailored to the knowledge of experts can save you a few detours and a lot of time.

At the same time, you have to understand that the types of tours offered are very different and there is a huge repertoire for tourists with all kinds of interests. For example, the mob and gangster tours are some of the most entertaining on offer locally, as they take you to the corners of the city that became crime scenes during the days when the mafia took over the city.

Some tours are on tourist buses and others on minibuses, but you also have the option of seeing the city from above with spectacular helicopter tours of Chicago.

Details of interest:

  • Prices: prices are another advantage of these guided tours, as they cost on average between €25 and €40 per person, although helicopter flights are naturally more expensive.
  • Duration: it all depends on the itinerary you choose, but they vary between 3 and 5 hours in length, although this calculation is only an approximation.

Book the best tours of Chicago

2. Cruise along the shores of Lake Michigan and the banks of the Chicago River on a boat tour

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

Chicago is located at the southern end of Lake Michigan, one of the five bodies of water that make up the Great Lakes system, which are distributed between the Canadian and US borders. The city's skyline has grown along this coastline, so it's a great idea to spend some of your time visiting some of the places 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 spots 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, making it an ideal place for a bike ride.

Navy Pier is another stop you can't miss if you want to explore the shores of Lake Michigan during 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, which is joined by a host of shops and free public parks.

As for the Chicago River, you should know that it 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 southward, thus preventing the pollution of Lake Michigan.

Riverwalk is a path that has been designed so that pedestrians can enjoy the riverbanks along much of its route through the city center. I recommend walking from the section of the bridge on N Columbus Dr. to the Franklin-Orleans Street Bridge.

But there are also cruises that tell you the history of Downtown, while highlighting the significance of each of the skyscrapers and drawbridges in the area. :::link|text=Cruises on Lake Michigan|element=sc-22-1199::: are another highly recommended entertainment option after a morning of touring the urban heart of the city.

  • **Learn more...**If you want to know more about water tours in Chicago, check out this article on :::link|text=Lake Michigan cruises|element=sc-22-1199:::.

Book a cruise on Lake Michigan

3. Spend an afternoon immersed in art at the Chicago Art Institute

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

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

Grant Wood's American Gothic, Seurat's Afternoon on the Island of Grande Jette, and Van Gogh's self-portrait are just some of the great highlights of this museum. It has the highest 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 solid collection of Byzantine works, as well as African art and contemporary and modernist works.

Other iconic buildings such as the Chicago Symphony Orchestra are located in the vicinity of this museum. It's not a bad idea to get your tickets through one of the Chicago tourist attraction passes so you can enjoy the best museums in Chicago.

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

  • **Learn more...**If you want to know more about this type of site, check out the article :::link|text=on tickets to the Museum of Contemporary Art Chicago|element=sc-22-1199:::.

Book a visit to the Art Institute of Chicago

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

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

The Willis Tower is a place that is automatically associated with Chicago's architectural identity, due to the fact that this 110-story skyscraper was 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 even though it is no longer called the Sears Tower and is now officially known as the Willis Tower, it continues to be an important space for this community.

You have the opportunity to experience this building in a rather unique way, as there is an observation deck on the 103rd floor that allows you to stand in glass cubes that literally place you above the cityscape.

The observation deck is known as the Skydeck, and the glass ledges are called The Ledge. On a clear day, you will have the opportunity to see the entire city in a panoramic view, and your visibility will extend to the well-known suburbs of the Chicago Metropolitan Area.

Details of interest:

  • Prices: Tickets to the Willis Tower Skydeck usually cost around €30 for adults and €20 or €25 for children. I recommend buying your tickets in advance if you want to guarantee a spot for the hours you have available for this activity during your day.
  • Hours: It is open every day of the week and stays open until 9:00 p.m. This makes sense, considering that enjoying this beautiful view is one of the best things to do in Chicago at night if you are looking for a family-friendly activity.

Book a visit to the Chicago Skydeck at Willis Tower

5. Take a guided tour of Chicago on a Segway

People on Segways| ©ivecanski
People on Segways| ©ivecanski

If you want to admire the Museum Campus and Lake Chicago, 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 can enjoy the same sights as when you walk.

An expert guide will tell you stories and interesting facts about the city or the places you will pass by. You'll take a 7- or 8-mile Segway tour to see various sites such as Soldier Field, home of the Chicago Bears.

Book a guided Segway tour of 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 seeing the Chicago skyline is something you can't miss if you're visiting this modern city. This tour lasts 45 minutes, which is more than enough time to take some epic photos.

You should also know that the tour includes noise-canceling headphones and commentary from a guide. This tour is a great option for three passengers, so you can go with your family or friends.

  • **Learn more...**If you want to know more about this type of activity, check out this article on the best helicopter tours.

Book a helicopter tour of Chicago

7. Purchase the Chicago CityPASS and visit a variety of impressive sites

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

In case you didn't know, the Chicago CityPASS offers tickets to several tourist attractions in the city. For example, Skydeck Chicago, Shedd Aquarium, Field Museum, and other sites. The purpose of this pass is to save up to 50% on tickets to popular attractions.

Other sites you can visit with this pass include Chicago's 360 Observatory and the Art Institute of Chicago. You even have the option of visiting 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's major sights by minibus, this could be the best option for you. It's a small group tour with stops at major tourist attractions. Bring your camera or drone to take photos and record exciting videos.

Among the sites you'll see are: The Rookery skyscraper, Millennium Park, Museum Campus, Buckingham Fountain, Magnificent Mile, Chicago River, Lincoln Park, and Gold Coast. You'll 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 city's great wonders

Museum skeleton| ©tagbuzzard
Museum skeleton| ©tagbuzzard

Continuing with 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 it houses the largest Tyrannosaurus Rex ever unearthed, making it a must-see for lovers of the curiosities of our planet Earth.

It is truly one of the largest museums in the world in terms of the breadth of its exhibits and the type of approaches taken by its curators. There, you will learn about the different ecosystems that make up life on the planet, while also accessing various exhibits on the history of ancient and modern societies.

Details of interest:

  • Prices: If you are interested in purchasing tickets to the Field Museum of Natural History in Chicago, you should know that prices are around €30 per adult for general admission and €36 or €38 for admission that also includes access to the 3D cinema on the premises. Children between the ages of 5 and 18 receive a discount of approximately 10%.

  • Hours: Open daily from 9 a.m. to 5 p.m. Keep in mind that it will take you approximately 4 hours to see all the exhibits.

  • **Learn more...**If you want to know more about this activity, read the article on 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

Over the years, each city begins to develop its own unique gastronomic universe. This is also influenced by the historical and cultural events that shape the growth of society in terms 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 cuisine that resulted from the mixing of these populations in this beautiful city.

Eating Chicago-style pizza, sampling hot dogs as interpreted by the locals, and sitting in a bar drinking authentic Irish beer are just some of the activities that could be part of these gastronomic tours of the city. These tours come in many different formats to suit all types of tourists.

For example, some tours focus exclusively on visiting the best donut shops in the city, while others combine a cycling tour with stops at the most iconic restaurants in the area. As long as they are dedicated to preparing these dishes that have been enhanced with Chicago's gastronomic style.

Keep in mind that most of the best food tours in Chicago tend to take place early in the morning or after noon, and that prices vary depending on the type of activity. Obviously, tours that include bike rental and a couple of food stops tend to be more expensive than walking tours that only cover a radius of two or three kilometers.

Details of interest:

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

  • Duration: It is uncommon for a food tour to last longer than three hours, but it is also unusual for them to last less than one 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 of Chicago

11. Admire the city's architecture as you stroll along the Chicago River

Boats on the river with views of the buildings| ©Victor Silas
Boats on the river with views of the buildings| ©Victor Silas

A stroll along the magnificent 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 beautiful views. In addition, on this tour you will enjoy commentary from an architecture expert, so you can 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 so you can take unforgettable photos and post them on Instagram and other social media. Keep in mind that this tour lasts 1 hour and 15 minutes, so you can visit other tourist sites on the same day.

Book a Chicago River cruise

12. Stop at Union Station

train station| ©Luis Leon
train station| ©Luis Leon

If you like historic buildings and are passionate about everything to do with railways, then you have to visit Union Station. It is the most important station in the United States public train system for the Midwest region, and its internal train storage configuration is so large that it extends underground for 9 city blocks.

The structure of the building is quite iconic, and for this simple reason alone, it is an interesting destination to include in your sightseeing plans. The marble floors, wide staircases, and neoclassical architectural finishes also make it one of the last spaces that adequately preserves the beauty of American train stations from the last century.

If you are traveling in December, this is a great place to include in your plans for things to see and do in Chicago during Christmas. This is because it is decorated in all the splendor of the holiday season, making it an ideal location for a first-class photo shoot.

13. Take a nighttime ride on a BIGBUS through Chicago

BIGBUS at night| ©Matt Taylor
BIGBUS at night| ©Matt Taylor

The BIGBUS has an open-top second floor, so you can get a better view of the city at night and enjoy the lights of the shops and impressive skyscrapers. Keep in mind that the BIGBUS passes by the Campus Museum, from where you can see the illuminated Chicago skyline.

One of the stops is the Tribune Tower, where you can enjoy beautiful views at dusk. Another stop on 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 your ticket for the Chicago Big Bus

14. Tour Lake Michigan on a speedboat

Boat on the lake| ©West Osee
Boat on the lake| ©West Osee

I invite you to hop on a 2,000 horsepower speedboat to tour the vast and beautiful Lake Michigan. This activity combines natural landscapes and incredible urban views of the city of Chicago.

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

Book a cruise 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 Chicago's most notable breweries. Among them, I can mention a craft beer production company, so you can see how this delicious drink is made.

In total, this tour offers visits to three popular breweries in the Windy City. In addition, the package includes 45 to 55 ounces of craft beer and a beer barrel-shaped bus. Do you like beer? In Chicago, you'll taste excellent local beers.

Book a Chicago craft beer tour

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

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

Chicago's Loop district has a lot of history, for example, various local mobsters have passed through there and left their mark on the city. You'll hear stories and anecdotes about gangsters and ghosts, two topics at a low cost.

Similarly, a guide will tell you spooky stories about the district and show you various haunted sites that you'll never forget. This is definitely an activity you can enjoy at any time of the year.

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 what may be your favorite team, the Chicago White Sox. Cheer and shout to support your MLB team; the excitement among thousands of baseball fans is impressive.

All games are played at Guaranteed Rate Field, the stadium and home of the Chicago White Sox. Not only will you see your team play, but also 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 play in their hometown.

Book baseball tickets in Chicago

18. Visit Millennium Park and see the 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 its extensive green spaces and the modernity that characterizes these public parks. Millennium Park is one of the most iconic of all, and its proximity to the city's financial and tourist center makes it a must-see during the first few days of your trip.

It was inaugurated in 2004, and since then, its 10 hectares filled with modern and abstract sculptures have served as a gateway to what has become the city's downtown.

There you will find all kinds of iconic elements of architecture and art, with the concert pavilion designed by the talented architect Frank Gehry as the star of the show. If you are lucky, you will probably find a band playing live music, as this public space strives to remain an interesting place for tourists and locals alike.

However, the attraction that undoubtedly steals the show at this site is the Cloud Gate sculpture, which was designed by Anish Kapoor and is now known as The Bean because of its curious structure that resembles a giant, reflective metal 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 for the morning, followed by a tour of the Chicago River skyscraper area.

As this park is located right in the middle of several kilometers of public spaces along the Monroe Harbor coastline, it is also advisable to take part in the best Segway tours in Chicago.

These modern skateboards can take you from Millennium Park to Buckingham Fountain or Grant Park, which are other beautiful places worth visiting on a morning of outdoor walks.

Book a Segway tour of Chicago

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, interestingly, it is the oldest planetarium in the United States. It was inaugurated in 1930 and currently combines technological shows about outer space with permanent exhibitions of ancient astronomical instruments and all kinds of books on this interesting branch of science.

There are also exhibitions on the Apollo 11 moon landing, and if you wish, you can travel back to the beginning of the last century to see what the Chicago sky looked like before the excessive light pollution that characterizes large modern metropolises.

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. It is also a lot of fun for the whole family.

Its location on the shores of Lake Michigan is also privileged, as it is in the same area of public parks as the Shedd Aquarium and the Field Museum of Natural History. These are other family entertainment alternatives that you can visit on other days of your trip or even on the same day if you organize your itinerary to visit them one after the other.

Details of interest:

  • Prices: prices range from €20 to €35 per adult, depending on the number of audiovisual shows you have access to. The cheapest ticket only includes admission to the planetarium museum.
  • Hours: Open every day of the week from 9 a.m. to 9 p.m., except on Wednesdays when it stays open until 10 p.m. There are special hours during peak tourist seasons.

20. Marvel at the beauty of the Chicago Theatre

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

If you've done a little research on theaters that are influential in 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 is 6 meters 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, functioned as a cinema for screening silent films. Over time, it has become a more complete space and today it is used for theatrical productions as well as live concerts.

You can explore it with one of the guided tours that take place every noon, which is a great opportunity to learn firsthand about the secrets that have been kept in this building since the days when artists such as Frank Sinatra performed in front of large crowds inside.

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

21. Hire a hop-on hop-off bus in Chicago

People on the Tour| ©Dan Gaken
People on the Tour| ©Dan Gaken

A hop-on hop-off bus tour should be on your Chicago bucket list, as it gives you the opportunity to visit the sites you want, such as the Chicago River, Willis Tower, Adler Planetarium, and Cloud Gate. You decide whether to 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, making this a fairly comprehensive tour of the city of Chicago.

Book a hop-on hop-off bus tour of 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 Wrigley Field, the major league baseball stadium, especially if you'd like to see a Chicago Cubs game. This baseball stadium was built in 1914 and has a capacity of 41,160 people for games and 41,847 spectators for concerts.

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

Book tickets for the Chicago Cubs

23. See the city from a 360º observation deck

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

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

From the observatory, you can enjoy beautiful views and take in the Chicago skyline. You can also opt for an exemplary view of the city from a tilting platform (TILT). The latter option is 305 meters high.

24. Dine on a cruise and enjoy incredible views of Chicago

people seated at a table on a cruise| ©Kelly
people seated at a table on a cruise| ©Kelly

This is a 3-course dinner on Lake Michigan. What's more, the dinner takes place on a beautiful Chicago cruise ship, so you can admire the local architecture 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 bring drinks with you to quench your thirst or warm up. In addition, the tour lasts an average of 2.5 hours.

Book the dinner cruise in Chicago

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

Two people cycling along the lake| ©Chait Goli
Two people cycling along the lake| ©Chait Goli

With this tour, you can cycle up to 22 km through the Windy City. The tour also includes stops at craft breweries and high-quality local food shops. In other words, in just 4 hours you can sample 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 any more money on different tickets. You only have to pay for admission to Wrigley Field.

Book a bike tour of Chicago

26. Enjoy Chicago's fascinating Art Deco

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

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

For example, you can enjoy 1920s Jazz Deco and Chicago's Modern Art buildings. The tour also includes admission to the Chicago Architecture Center, where you can see various 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 a street painting experience that opens your mind and helps you unleash your inner creativity. The school provides a workshop with local artists where you can create your own artwork.

Using spray paint or stencils, you will create your BYOB painting alongside an expert teacher or guide. At the end of the workshop, you can take your artwork home with you. The workshop includes painting materials and the canvas you will take home.

Book a street art workshop in Chicago

28. Learn about the history of literature at the Museum of American Writers

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

Learn about the history of poets and sports writers, as well as their places of origin. Also, learn about the houses affiliated with this museum in Writers Hall. Other aspects to explore include galleries such as Wintrust Chicago and The Mind of Writers.

At the Wintrust Chicago gallery, you will find important information about local writers and their literary style. You should also visit 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 a true pizza lover? Well, on this tour you can discover some of Chicago's favorite pizzerias. For example, Pizano's Pizza and Flo & Santo's, two legendary local pizzerias. Interestingly, the former has been in business since 1943.

Another pizzeria you can visit on this food tour is Pequod's, a pizza legend thanks to its layer of caramelized cheese. You can also visit Coalfire, a place that sells cakes baked with charcoal.

Book a pizza tour in Chicago

30. Enter the world of crime in Chicago

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

Hear stories about Al Capone and the Untouchables, as well as the Chicago mafia. Chicago's mobsters committed many crimes, and you'll investigate them with a professional guide and driver. That means you'll have live commentary on the bus.

You can also take photos from the bus of various crime scenes, which makes the activity much more complete. And, as if that weren't enough, you'll enjoy climate-controlled temperatures.

Book a crime tour in Chicago

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 drunk actor performing a Shakespeare play? Well, you've come to the right place. Here, a professional artist with five shots of whiskey tries to perform in a high-level play. Yes, a drunk actor, as you read it. Sounds fun, right?

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

32. Go to a Chicago Bulls game

boy in red shirt| ©slevy15
boy in red shirt| ©slevy15

The Chicago Bulls are one of the best basketball teams in the NBA and play several games in their home city. With that in mind, you can't miss a basketball game. Basketball games in Chicago are usually held at the impressive United Center multi-sport arena.

What's more, at the United Center in Chicago you can see different NBA teams, so don't miss this opportunity. Best of all, you can buy tickets to a Chicago Bulls game throughout the year, 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 see contemporary art galleries at any time of the year. Admire the architecture of this spacious museum, which opened in 1967. Inside, there are various events for all audiences. However, you must pay to attend some of them.

Keep in mind that you can see various works by artists who are still alive, that is, artists of our time. The museum also has a shop, restaurant, and bar, so you can enjoy a unique experience eating among incredible art galleries or simply buying a souvenir.

34. Take a street art tour of Chicago

Street art| ©Daniel Lobo
Street art| ©Daniel Lobo

Although many people overlook Chicago's street art, this walking tour will take you to the city's most artistic and iconic streets. Murals, small graffiti, and contemporary street art will leave you speechless with their colorful designs.

The technique of street artists can be seen on streets such as 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'll enjoy a stop at the Ipsento café.

Book a street art tour of Chicago

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

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

In River North, you can enjoy a 60-minute escape game. There are several options to choose from, such as the game "Gold Rush," in which you must find gold to win. There is also a game called "Special Operations," in which you become a secret agent and solve a complex case.

Another game offered by this tour is "Prison Break, " in which you must escape from prison any way you can. As if that weren't 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 at the best places in Chinatown

entrance to a Chinese restaurant| ©edwardhblake
entrance to a Chinese restaurant| ©edwardhblake

Without a doubt, one of the neighborhoods where you'll find excellent cuisine in Chicago is Chinatown. This Chinatown is one of nine Chinatowns in the United States. The Asian-style houses and shops will surprise you, so bring a good camera to take pictures.

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

37. Walk through the Medieval Torture Museum

informative museum poster| ©Doss
informative museum poster| ©Doss

In this museum, you can see different torture tools , macabre interrogations, and methods of immobilizing people. In addition, there are various wax figures of murderers with their bloody victims, showing the atrocious tortures that existed at some point in history.

You will also enjoy clear and informative audio commentary on each torture device. This site is 6,000 square feet in size, so you will be able to see different aspects related to torture in medieval times.

Book tickets for the Medieval Torture Museum

38. Eat delicious donuts in Chicago

doughnut with coffee| ©Thomas Hawk
doughnut with coffee| ©Thomas Hawk

Since there are many people like me who love donuts, I recommend the incredible Underground Donuts tour. On this tour, you will enjoy tasting delicious donuts at Chicago favorites such as Dappeer Doughnuts, Firecakes, Do-Rite Donuts, Stans, and Doughnut Vault.

And don't worry, there are also vegan and gluten-free donuts, as well as traditional donuts with all the ingredients. You must inform the tour organizers in advance so that they can accommodate your requirements.

Book the Chicago Donut Tour

39. Spend a pleasant afternoon in the Navy Pier area

Navy Pier seen from afar| ©Gio Mag
Navy Pier seen from afar| ©Gio Mag

The Navy Pier area (on the shores of Lake Michigan) offers a variety of entertainment options for a pleasant afternoon with your family or friends. From mechanical attractions for adults and children to live music.

You can also buy clothes and food here, thanks to its various fashion stores and restaurants. In addition, Navy Pier offers free dance, theater, and other cultural events. There are even fireworks on some occasions, so you'll have to wait until 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 an unparalleled experience, especially for lovers of Harley-Davidson, BMW, and Indian Pursuit bikes. The good news is that you don't have to buy these types of motorcycles; you can just rent them.

At Rental Motor Bike, you can choose the motorcycle you like best. By the way, another of my favorite motorcycle models for riding around Chicago is the Honda Goldwing 1800, apart from models such as the Harley-Davidson Pan America 1250, of course. Are you up for riding a motorcycle around Chicago?

41. Feast your eyes on Michelangelo's works in Chicago

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

The Sintine Chapel Exhibit in Chicago has an immersive photo gallery of Michelangelo. This painter's works left a big mark on the Vatican, and now you can see high-resolution images of his epic paintings up close.

The people in charge of this site have held exhibitions on Star Trek and Titanic, so you can imagine the high quality of this activity. In fact, they have also held exhibitions on Michael Jackson and Frida Kahlo. If you like painting, be sure to visit this type of exhibition 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. It also has 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 visit their official website to learn more. And, of course, one of the favorite attractions at this zoo is that you can feed a giraffe. Yes, now your dream is possible.

43. Kayak on 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 paddle freely down the Chicago River. Stop for a moment if you want to admire the city's great architectural works 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. Sharpen 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 to Beyoncé, Queen, and Adele. All in a unique candlelit atmosphere that will relax your mind and sharpen your senses.

Some of the 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 the 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 masterful constructions, such as iconic city buildings in LEGO form.

At 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 are sure to love the world of LEGO as much as your children do.

46. Visit Frank Lloyd Wright's Home and Studio

People outside Frank Lloyd Wright's Studio| ©Joseph Hollick
People outside Frank Lloyd Wright's Studio| ©Joseph Hollick

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

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 afraid of jumping out of a plane? Don't worry, with this experience you can feel what skydiving is like indoors, as there are several skydiving entertainment centers in Chicago. It is a safe wind tunnel system with an expert guide who will explain how to position your body when falling from a plane (before releasing the parachute).

Keep in mind that your children can also participate in this activity, so the whole family can enjoy it together. One of the companies that offers this type of activity professionally is iFLY, located in Lincoln Park. There are also other tourist agencies that 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 come together. This activity is specially designed for children, but parents can join them and play together. One of the attractions of the place is a tree house, which children will undoubtedly love.

Another activity is Cloud Booster, where your children can exercise while running through a fun and safe mesh tunnel. In addition, since most children love dinosaurs, here they will find a dinosaur expedition and skeletons of these incredible animals. In fact, there are dinosaurs recreated in the style of Jurassic Park, so to speak.

49. Take photos at Cloud Gate (The Bean)

People around Cloud Gate| ©austin02
People around Cloud Gate| ©austin02

In 2004, the great artist Anish Kapoor created The Bean, one of the most impressive sculptures in the city of Chicago, which is completely free to visit. That's right, you don't have to pay to see this piece in AT&T Plaza, which is part of Millennium Park. This is an activity that is best enjoyed during the day, but some tourists like me prefer to go at night, as you can see the buildings and skyscrapers lit up, making it an ideal opportunity to take some epic photos.

However, whether you go during the day or at night, you will be able to see how Cloud Gate reflects the people around it, thanks to its smooth, mirror-like surface. Don't forget to visit the surrounding area and enjoy a delicious meal with your loved ones.

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

50. Take a dip at the Whealan Pool Aquatic Center

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

The Whealan Pool Aquatic Center offers fun for the whole family. It is a large pool with slides for all ages and water attractions designed for younger children.

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

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 visit the site from Monday to 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. Incidentally, the building measures approximately 18 x 55 meters, so it is quite spacious. It is worth noting that there are wheelchairs available inside for people with disabilities.

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 a variety of nightclubs, including some geared toward the gay community. For example, there is Smart Bar, which offers drag shows, exotic dancers, and a host of themed events such as Madonna, Prince, or Björk. There are also activities alluding to the 1980s.

But if you're not really interested in a nightclub for a gay audience, I recommend The Underground, which is a favorite among electronic music lovers. Of course, people of any sexual preference can enter this venue, but everyone must adhere to a dress code. Best of all, excellent DJs from around the world have performed there, and you may even spot a celebrity or two in the crowd.

On the other hand, there's the Smart Bar, which focuses on dance music, so dancing and drinking there will be a very enjoyable experience for lovers of this genre. In fact, famous DJs from around the world and, of course, the United States have played here.

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

entrance to Superdawg| ©Jim Hill
entrance to Superdawg| ©Jim Hill

The legendary Superdawg Drive-In restaurant awaits you if you're visiting Chicago. Here you'll find delicious hot dogs and hamburgers.

You can also buy drinks and side dishes (such as French fries). Luckily, you can do everything from your car, which is a great option if you don't want to pay for parking. The customer service staff will treat you very well and answer any questions you may have when placing your order. Simply drive up to the ticket window in 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

The Chicago History Museum has collections from various designers who have made their mark on 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.

Similarly, here you will learn about the history of Chicago and, if you wish, you can hire a local expert guide to explore the city from a historical perspective. Usually, around Halloween, there are some haunted events that will entertain 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 Latin culture at the National Museum of Mexican Art

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

Latin 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 on the history of Mexico and aspects of the border with the United States. In this collection, you will see Mesoamerican objects, folk 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 jet ski| ©fjsmalaga
person on jet ski| ©fjsmalaga

Want to ride a Yamaha VX110 jet ski on Lake Michigan? Well, this activity is waiting for you, offering jet skis in excellent condition and essential accessories such as life jackets and seat belts. This way, you can admire the Windy City from the water.

Keep in mind that you can rent a jet ski at Jet Ski, and you can even take lessons with a professional from the company before riding 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

entrance to the zoo| ©Jack
entrance to the zoo| ©Jack

At Lincoln Park Zoo, you can see a variety of wild and exotic animals from a safe distance. Among the animals are rhinos, red pandas, hippos, and Japanese macaques. There are also other animals such as Jamaican iguanas and African penguins.

In total, there are approximately 200 different species of animals, making it a wonderful experience for couples or the whole family. You will also find gardens with more than 1,200 species, including 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 event that usually takes place annually around Labor Day. The festival lasts between 8 and 9 days.

Jazz concerts are held at various locations throughout the city, and admission is free. Some of the venues that typically host live performances include The South Side Jazz Coalition, Constellation, Sleeping Village, Hungry Brain, Live the Spirit Residency, and The Birdhouse Inc. However, be sure to check the complete schedule before traveling.

59. Get tipsy at Chicago's rooftop bars

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

Cocktails and other drinks await you at Chicago's fabulous rooftop bars. I'll start with Z Bar, but not because it's the best or worst, as I really like all three options I recommend here. Z Bar is very eye-catching at first glance, so it's a spectacular place for photos or selfies of the city. There you'll find high-quality food and drinks.

Another rooftop bar you absolutely must visit is Cerise Rooftop, which offers live music with excellent local DJs and is also close to your room if you decide to stay at Virgin Hotels Chicago.

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

60. Enter the Ernest Hemingway Birthplace Museum

beige building with green| ©Irina Hynes
beige building with green| ©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 Queen Anne style, so it is a popular site for tourists and students due to its architectural significance.

The house was built in 1890 and was the first in Oak Park to have electricity. If you enter the museum, you can admire both the period interior design and the antique furniture. And, of course, in this house you will hear stories about this incredible 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 pays tribute to African American figures who left their mark on the country. You will also see stories about Africans who came to the United States during the era of slavery.

Similarly, you will find antique furniture that was and still is important to the history of African American culture. Among its collections is a watercolor painting by Charles C. Dawson. You will even find a painting of George Washington Carver in a laboratory.

62. Experience sunset on a boat

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 various boat tours available, so you can also choose from a variety of boats (sailboat, cruise ship, motorboat, etc.). Without a doubt, this is a special activity that you should experience with your partner. Add a glass of wine or a delicious appetizer to make it even more enjoyable.

Similarly, there are boats that include a trip to see the fireworks in the Navy Pier area. If you know how to sail or want a private sailboat, you can even rent one; in Chicago, almost anything is possible. Here you can check out the different sunset boat tours. This type of activity will leave couples with fond memories of 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 winter. It is a large rink with safety bars on the sides. You can skate for free if you bring your own skates. However, to enjoy free skating, you should check the schedule on the website, as free skating is not allowed at certain times of the day.

You can also rent skates if you don't have your own, so you can definitely enjoy ice skating at Maggie Daley Park. Another important thing to know about this activity is that the park has other attractions for the whole family, including a food stand.

64. Enjoy a delicious ice cream at Rainbow Cone

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

There is an excellent local ice cream shop in Chicago called Rainbow Cone. If you like ice cream, you should visit it to try its unique and delicious flavors. One of my favorite ice creams is the Original Rainbow Cone, which has five flavors: chocolate, orange sherbet, Palmer House, pistachio, and strawberry. In other words, this ice cream is the house specialty.

In addition, at this local ice cream shop, you can enjoy mini donuts with coffee, a recent addition to their extensive menu. Another delicious treat is the chocolate cake with the five rainbow flavors. You will undoubtedly feel like a kid eating candy at this ice cream shop. By the way, you can go to Rainbow Cone with the whole family without any problems.

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 main 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, Buddy Guy's Legends hosts many national and international blues and jazz concerts.

And, as you would expect 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're a fan of the genre, you've surely heard his music.

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

66. Cheer on the Chicago Blackhawks hockey team

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

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

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

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 are held between June, July, and August, but only on Mondays and Thursdays. Don't miss the musical activities if you're going to Chicago during these months of the year.

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

Some of the artists who have performed there include Abigail Washburn, Gabriel Garzón Montano, Brandi Clark, Samantha Crain, the 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 stunts at the Chicago Air & Water Show

group of planes performing acrobatics| ©didimouman
group of planes performing acrobatics| ©didimouman

This free event is organized by the city of Chicago and features a series of planes and expert pilots performing acrobatics over Lake Michigan and North Ave. Beach. You should also know that this is the largest aerial acrobatics event in the United States.

How much does it cost? Don't worry about the price, as the event is completely free and you can watch it from anywhere on the shore of Lake Michigan. When does it take place? It is usually held in the summer (August) so that the stunts can be seen better in the clear sky. Bring your umbrella to protect yourself 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 eight glass-enclosed gardens will leave you speechless, as they feature thousands of plants from around the world. The most impressive thing is that the plants are behind glass, so they are better preserved. This is known as landscape art under glass.

In addition, this botanical conservatory has various natural environments for children and a water lily pond. This site also has 10 acres of gardens open to the whole family. 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 as you watch the various faces of the Crown Fountain

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

Visiting the Crown Fountain in Millennium Park will allow you to enjoy incredible urban views while laughing at the funny faces in the video sculpture. This fountain was designed by Spanish artist Jaume Plensa and built by Krueck and Sexton Architects. Keep in mind that the work was inaugurated in July 2004.

The fountain has two towers or video sculptures at each end and a sheet of water on the ground. You can walk around the entire fountain, get your feet wet, and admire the faces of people opening their mouths up close. 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 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 valuable monuments. It was designed by British-American artist Edward H. Bennett. The monument was inspired by the Latona Fountain.

It is worth noting that in this work you can see small horse-shaped statues where the water comes out. Although you can admire this impressive work during the day, I also recommend seeing it at night, as it features a colorful and striking light show. Don't wait any longer to go see it and take a few photos in front of it.

Check the address of Buckingham Fountain and plan a visit. Luckily, it is a public fountain, so there is no admission fee or taxes.

72. Marvel at a Broadway show in Chicago

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

The James M. Nederlander Theater is the official home of various Broadway shows in Chicago. This theater was inaugurated in May 1926 and features the architectural style of the era.

The first "Broadway in Chicago" play performed at this theater was Wicked, which ran for three long years. In 2019, it was named after Broadway founder James M. Nederlander. Today, it continues to be the home of Broadway shows in the Windy City, so you can check their website to plan your visit to the theater.

Some of the events that have been held there are ** The Lion King, Les Misérables, and Disney's Aladdin**. Do you like Broadway plays and musicals? You can also see some shows in Chicago.

73. Sing and shout at the Lollapalooza Festival

People gathered at the concert venue| © Danny Howe
People gathered at the concert venue| © Danny Howe

If you like music festivals with a variety of genres, I recommend Lollapalooza, which takes place every day in July in Chicago. The most popular music genres at this festival are rock, punk rock, metal, and electronic. Be sure to 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 is held in Grand Park, so you have a variety of accommodation options nearby. Be sure to keep an eye out for ticket sales so you don't miss out, as it's difficult to buy tickets as the festival date approaches.

74. Visit the Museum of Science and Industry

museum admission| ©Paul_Henry_
museum admission| ©Paul_Henry_

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

One of the attractions at this museum is a five-story screen for the world of cinema. And, of course, my favorite attraction is the German U-505 submarine from World War II. This submarine will give you goosebumps with its excellent design and the story that brought it to the United States. Interestingly, the U-505 is the only German submarine in the country.

75. Be amazed 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 and orchestra artists. In addition, at this venue 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 hear the music being played on stage clearly. By the way, the Lyric Opera of Chicago not only offers live music, but also educational and innovative activities.

76. Experience delicious and 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 best 3-Michelin-starred restaurants in the United States. So, if you're into unique food prepared by national and international chefs, 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 US according to Gourmet and Business Insider and "Best Restaurant in the World" by Elite Traveler. Without a doubt, the dishes you will try here are a culinary work of art. You can make a reservation on their official website. Don't wait any longer to eat at Alinea Restaurant!

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

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

Children will have the time of their lives at 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 upper deck of the pirate ship, you'll find a birthday party room. There's also a place called Cannonball Falls for picnics. In fact, this area is so large that it can accommodate five birthday parties at once. However, Cannonball Falls is available for full reservation on Thursdays, Saturdays, and Sundays from 5:00 p.m. to 8:00 p.m.

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

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

If you're going to Chicago in June or July, don't miss the Taste of Chicago food festival. This festival takes place at different locations 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 is only held on Saturdays, which is something to keep in mind before your visit to Chicago. Also, don't worry about parking your car, 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 site is a plus for the whole family, as it has children's attractions and butterfly gardens for people of all 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 children to this museum where they can learn while having fun.

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

80. Walk through Bloomingdale's and shop for a variety of products

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

At Bloomingdale's in Chicago, you'll 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 being sold there for the first time. Bloomingdale's also offers various beauty and personal care services.

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

81. Learn at the Richard H. Driehaus Museum

Lighted chandelier| ©Stephanie Barto
Lighted chandelier| ©Stephanie Barto

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

You should also know that the museum offers an app for iOS and Android, which allows you to take self-guided tours of the three floors. We recommend visiting the museum in person for a more immersive experience. Your mobile device must have internet data, as there is no free WiFi network available.

Other things to keep in mind are to download the app before going to the museum and to bring headphones or earphones with you. This is because the app offers excellent audio that will guide you through the museum.

82. Enjoy jazz in all its glory at The Green Mill

music group playing| ©rebecca anne
music group playing| ©rebecca anne

Enjoy an authentic jazz experience at The Green Mill, a bar that features the best local jazz bands and artists, as well as foreign artists on special occasions. There are performances every day, so if you go to Chicago, you're sure to be able to have a drink while listening to good music at the bar.

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

83. Get a relaxing massage at a Chicago spa

woman receiving a facial| ©Raphael Lovaski
woman receiving a facial| ©Raphael Lovaski

As you might expect, Chicago has many luxurious, refreshing, and relaxing spas, 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 to by people who specialize in skin treatments and massages. It's not for nothing that it's known as Chicago's urban oasis.

Relax your mind, body, and spirit like never before at this wonderful luxury spa where you'll be immersed in Asian and Ayurvedic philosophy. Some of the experiences offered by the spa include natural stone massages, aromatic oils, and the popular Marma massage.

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

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

Another must-see activity in Chicago is a Chicago Bears game. This American football team usually plays in its home city, specifically at the multipurpose Soldier Field stadium. Games are held on various dates each year, so be sure to check the official Chicago Bears website to stay up to date and purchase tickets in advance.

This monumental football stadium has also been the venue for many concerts by famous national and international artists. One of the most striking things for locals and visitors alike is the sheer size of Soldier Field and the adrenaline rush you feel when cheering on your favorite team alongside thousands of people around you.

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

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

Looking for a restaurant where you don't have to make reservations to visit? You've come to the right place. Au Cheval Restaurant does not require reservations; seating is on a first-come, first-served basis. There you can eat burgers with beef and smoked bacon.

At Au Cheval, you should also try the Bologna, which is one of the main ingredients in their recipes. Not only can you eat delicious food at this restaurant, but they also have all kinds of drinks, making the experience even more enjoyable. Don't forget to arrive early to avoid the lines.

86. Head to Dusty Groove to buy vinyl records

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

This place is like paradise for CD and vinyl collectors, as you can find original albums from various retro bands and artists, as well as from the present day. Rock, funk, soul, and hip hop are just some of the musical genres in stock. There are thousands of vinyl records from all over the world, including rare or little-known albums.

You can view the vinyl catalog on the official Dusty Groove website, and you can even buy online, as the company ships nationally and internationally. There are constantly new vinyl records in their library, so you may find the one you've been searching for everywhere else.

87. Try different specialties at Time Out Market

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

Try food from various regions of the world or various well-known brands here at the Time Out Market in Chicago. The site also has a 50,000-square-foot hall where you can not only eat, but also enjoy live music. The venue also hosts other activities for children and even yoga.

Similarly, this venue offers excellent services for work groups, birthdays, or semi-private gatherings 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, burgers, hot dogs, desserts, salads, and more.

88. Be amazed by a concert by the Chicago Symphony Orchestra

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

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

In addition, 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 presented are Prokofiev's Sixth, Rachmaninoff'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.

Hurry and get your ticket for the Chicago Symphony Orchestra and enjoy a different experience that will take you away from your daily routine.

89. Discover various archaeological finds at the Oriental Institute of Chicago

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

Another activity you shouldn't 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 Edgar and Deborah Jannotta Mesopotamian Gallery, The Henrietta Herbolsheimer MD Syro-Anatolian Gallery, The Robert and Deborah Aliber Persian Gallery, The Robert F. Picken Family Nubian Gallery, etc. Picken Family Gallery, the Joseph and Mary Grimshaw Egyptian Gallery, and more.

For example, in Joseph's gallery, you can see 800 objects from the Predynastic Period to the Byzantine Period, including a 17-foot-tall statue of King Tutankhamun at the entrance to the gallery. Similarly, in the Yelda Khorsabad courtyard, the most incredible objects you will see are the 16-foot-tall Human and the Winged Bull's Head.

90. Cheer on the Chicago Fire team at Soldier Field

Who doesn't like soccer? If you're a fan, cheer on the Chicago Fire club at Soldier Field, a multi-purpose stadium with a capacity of 61,500 spectators. An interesting fact is that it was built in honor of those who died in World War I.

Without a doubt, it will be an unforgettable experience to be in this stadium alongside the locals and support their team. To purchase tickets for the games, here is the official website of the Chicago Fire Soccer Club.

91. Ride the roller coasters at Six Flags Great America

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

Feel like a kid again enjoying the attractions at Six Flags Great America, especially its 15 roller coasters, and let all your inner adrenaline out. You can also enjoy this experience with your family, as there are three children's themed areas, spectacular shows, and an incredible 20-acre water park.

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

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

Hard Rock Café| ©Philippe Reichert
Hard Rock Café| ©Philippe Reichert

This iconic venue is located in the River North neighborhood. Not only can you have a few drinks there, but you'll also see incredible pieces from music legends such as Jimi Hendrix, Billy Joel, Prince, and Buddy Guy on the walls.

You also have different dining options such as burgers, bruschettas, wings, classic nachos, sandwiches, salads, ribs, fajitas, brownies with hot fudge, ice cream, cheesecake, as well as a children's menu.

If you are interested in this place, I recommend purchasing a ticket to the Hard Rock Café in Chicago online before you travel, as you need to be sure of its availability before boarding 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 the favorite beach for locals and tourists of all ages. This is Oak Street Beach, where you can sunbathe 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, the beach is sometimes closed.

How attractive is this beach? Well, the beach itself is small, but it has spectacular views of the Chicago skyline, Lake Michigan, and various incredible buildings and skyscrapers. You can also see sports boats, cruise ships, and impressive sailboats in motion from the site. 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. Keep in mind that admission to this beach is free, but unfortunately, it is not very easy to find parking nearby.

94. Explore the Chicago Park District Golf

two boys playing golf| ©Kaleidoscope
two boys playing golf| ©Kaleidoscope

Golf in Chicago? Of course! This city is home to Chicago Park District Golf, which consists of several golf parks. There are even options for learning golf. The learning site I recommend is the Diversey Practice Center.

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

In any case, go to whichever golf course you like, as the district has a wide variety to choose from. For example, I haven't mentioned South Shore Golf Course or Robert A. Black.

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, inspiring the study of art and its conservation. Its collection is quite extensive, with an average of 16,000 objects to admire. You should also know thatit has works from 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 one of its events or exhibitions, but first check out its website for detailed information about its activities.

96. Gamble at the Horseshoe Casino Hammond

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

Gambling and games of chance are attractive to people from all over the world, so if you're in Chicago, you should visit the Horseshoe Hammond Casino. This casino is located next to Lake Michigan, on Casino Center Dr Hammond.

This casino is part of Caesars Entertainment, one of the best casino companies in the United States. Inside, there are various options such as table games and slot machines. You can also enjoy a restaurant where you can 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 historic site where you can find the Administration-Clock Tower Building, which features 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. You should also visit the National A. Philip Randolph Pullman Porter Museum, where you can enjoy permanent and multimedia exhibits.

98. Stop by Chicago's skateboarding parks

boy with skateboard in the air| ©Giovanna Gomes
boy with skateboard in the air| ©Giovanna Gomes

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

Another place you should check out is the Skate Park on Sacramento Ave. If you skateboard, practice there, as it has different rails, stairs, and platforms for performing tricks. I also recommend spending some time at Wilson Skate Park, one of the most visited skate parks by local athletes. Here you can see different people doing tricks on their skateboards.

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

99. Go paddleboarding (SUP) in Chicago

man paddleboarding| ©JGiacomino
man paddleboarding| ©JGiacomino

If you want to try SUP (stand-up paddleboarding) 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.

SUP sessions are usually held on the calm waters of Lake Michigan, a perfect place to learn this water sport. What's more, the boards and paddles are of high quality; for example, the paddle is made of F2 polycarbonate. Of course, this activity gives you the opportunity to admire the city of Chicago from the water, meaning you'll have breathtaking views during your session.

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 to the city. The agency React Presents has been organizing this event for several years and has brought DJs from around the world.

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

If you want to know more about this great event in Chicago (dates, times, lineup, and more), visit its official website.

Reviews from other travellers

4.7
· 24977 Reviews
  • L
    L. X.
    5
    (0 Reviews)
    The overall experience was good, the food was delicious, but I think the service could be faster.
  • X
    X. D.
    5
    (0 Reviews)
    The food was amazing and the atmosphere very authentic, a great experience in the heart of Chicago!
  • Z
    Z. F.
    5
    (0 Reviews)
    I loved the food and the atmosphere, I felt like a rock star. I always wanted to visit this place since I was a teenager.
  • L
    L. E.
    5
    (0 Reviews)
    The food at Hard Rock Café is very tasty and the place is super cool. I had a great time, I want to come back!
  • J
    J. H.
    5
    (0 Reviews)
    The experience of cycling around the city was amazing, but it would be ideal if they offered more pick-up points.