Chicago City Tours

The city of Chicago is full of interesting activities and options for all tastes. Pack your bags and come with me to discover which are the best tours in the city.

Verónica Álvarez

Verónica Álvarez

10 min read

Chicago City Tours

Chicago | ©Bhargava Marripati

Chicago is one of the most important cities in the United States, as well as a tourist pole for its culture, gastronomy and entertainment activities. If you travel to it, you will be enchanted by its beauty and you will find a great number of things to see and do in Chicago. Not for nothing has it received the "Best Big City" award in the United States for five consecutive years.

Whether you intend to get to know its architecture, art, gastronomy and mysteries or if you prefer to discover the musical shows and nightlife in Chicago, in this article you have the guide to the best tours of the city to help you organize the ideal itinerary for you.

1. Chicago food tours

Flo & Santo's| ©Andrew Nawrocki
Flo & Santo's| ©Andrew Nawrocki

Chicago is a city that stands out for its varied international cuisine and also for being the birthplace of some typical American dishes that its inhabitants are proud of.

Being a very cosmopolitan city, the typical gastronomy of this region is characterized by having roots from different cultures. Traditional dishes are inspired by areas as far away as Europe or Asia, so Chicago's food is very rich in both ingredients and flavors.

What you can try on these tours

On Chicago food tours you can learn about the city's iconic gastronomic creations, such as the Chicago-style hot dog, which goes far beyond a simple sausage and bun and is a complete meal that will satisfy even the pickiest of eaters.

In the gastronomic tours of Chicago, you will also taste its famous pizza. I warn you that it is quite different from the one eaten in Europe and I must admit that at first I hesitated to try it, but after doing so I liked it a lot.

The Chicago style pizza or Deep Dish pizza, is characterized by having a thick dough and a fountain shape in which the different ingredients are placed (sauce, cheese, salami, etc.), looking more like a stuffed pizza than a traditional Italian style pizza.

Chicago's craft beer is also known for its quality and unmistakable flavor. You will also taste it in these very complete gastronomic tours around the city.

Finally, if you want to eat a local dessert, donuts are the most representative of the city.

Interesting details

  • Price: from 40 euros per person approximately.

  • Duration: between 2 to 4 hours depending on the tour you choose.

  • Means of transport: most are on foot, but there are also gastronomic tours by bicycle.

Book a food tour in Chicago

2. Segway tours in Chicago

During the Segway Tour| ©Ben Grey
During the Segway Tour| ©Ben Grey

If you enjoy riding a Segway, you can tour the city of Chicago in this way without any problems, since there are companies specialized in providing visitors with tours on this increasingly popular means of transportation.

Segway tours have become popular in several cities around the world thanks to their practicality and economy.

This type of vehicle allows you to travel a greater number of kilometers and also its size allows you to avoid the problems of congested traffic in larger cities, making it possible to optimize your time during the rides.

Segway tours in Chicago are an ideal way to see the city without having to walk a lot.

The guides of these tours have the certifications required by the city's legislation, which gives you more security.

You can choose between daytime tours, visiting the most famous places in the city such as Grant Park or Soldier Field, or take a night tour through the mysterious and haunted places of the city.

Details of interest

  • Price: from 73 euros per person.

  • Duration: about 2 hours.

  • Means of transport: segway.

Book your Segway tour in Chicago

3. Chicago sightseeing bus tours

Chicago's Big Bus| ©mbernero
Chicago's Big Bus| ©mbernero

Whenever I visit a new city, I always spend the first day of my stay touring it on a tour bus to get an overview and then delve into those places that I find most interesting.

The tour buses in Chicago, pass through all the places of interest in the city and, in addition, you can use them as a means of rapid transport from one place to another.

The value for money of the tickets of the tour buses is very good if you consider that the stops are free and you can get on as many times as you want during the validity of the pass you choose.

In addition, they offer audio guides so that you do not miss the details of the tour. These are in several languages, including Spanish, and are an excellent way to learn interesting facts about the main attractions of the city, which will help you choose which ones are worth visiting later with more time.

Details of interest

  • Price: from 45 euros per person.

  • Duration: the complete tour lasts 2 hours, but you can use it for the duration of the ticket as many times as you want.

  • Means of transport: bus.

Book the Chicago sightseeing bus

4. Cruises in Chicago

Chicago River Cruise| ©Kenn T.
Chicago River Cruise| ©Kenn T.

If you like sailing and want to see the city from another perspective, you can take a Chicago river cruise. On these tours you can sail on Lake Michigan, one of the 5 largest lakes in the world, and enjoy the views from the water.

You will have the option to choose between sailing during the day or at night. If you are traveling as a couple and want to have a romantic evening, you can opt for a night cruise with dinner included, you will not regret it, the views of the city are wonderful and the food is very good.

Sailing on Lake Michigan is something you can not miss, it is an incredible experience because the characteristics of this lake are totally different from others you may know.

Besides its huge size, it can have quite large waves at some times of the year, especially in winter and autumn, so it seems that you are sailing on the open sea.

Details of interest

  • Price: between 28 and 185 (option with dinner included) euros per person, depending on the duration and whether or not dinner is included.

  • Duration: between 40 minutes to 2 hours and a half.

  • Means of transport: boat.

Book your cruise in Chicago

5. Chicago Bike Tours

Biking in Chicago| ©Andy
Biking in Chicago| ©Andy

Another great way to see the city is by bike. Cycling enthusiasts are in luck with the wide range of bike tours available in Chicago.

While pedaling you can visit several important points such as the skyscrapers in Streetville or Lincoln Park and its surroundings by bike.

You can also take a food tour of Chicago by bike, so you can eat and burn off excess calories immediately.

Chicago bike tours include in the price the rental of all the necessary equipment for the excursion (bike and helmet).

Keep in mind that in this type of tour, as in those that can be done by segway, you have the advantage of traveling longer distances and also avoid traffic problems.

Interesting details

  • Price: from 52 euros per person approximately.

  • Duration: from 2 to 3 hours depending on the route.

  • Means of transport: bicycle.

Book your bike tour in Chicago

6. Tours to learn about Chicago's architecture

View from 360 Chicago| ©Janette Asche
View from 360 Chicago| ©Janette Asche

The buildings in Chicago are impressive, not in vain it is known as "the city of architecture". In the city, old and art deco buildings coexist with huge skyscrapers giving a very special attraction to the different neighborhoods, which does not go unnoticed by architecture enthusiasts and the general public.

There are several tour options that cover the most important places from an architectural point of view and are an excellent opportunity to get to know the city through the history told by its buildings.

By taking the guided tours through the best of Chicago's architecture you will learn why the constructive characteristics of this city are so famous.

From modern skyscrapers to art deco buildings, Chicago is home to architectural gems that make it a sought-after destination for architects and architecture students from around the world.

Details of interest

  • Price: from 27 euros per person.
  • Duration: about an hour and a half.
  • Means of transport: there are options on foot and also by boat.

Book your Chicago architecture tour

7. Chicago Gangster Tours

Gangsters and Ghosts Tour| ©GTE
Gangsters and Ghosts Tour| ©GTE

Another of the things that made Chicago famous were its gangsters, such as Al Capone or John Dillinger, who carried out their criminal activities in this city and were immortalized in series and movies.

If you want to know the history of the mafia and illustrious criminals of the city, you can do it in specialized tours on these topics, with guides who will tell you all the history and will take you to the places linked to the most famous gangsters.

Some of these tours are made during the night. If you are looking for things to do at night in Chicago you will find that there are several interesting options in the city.

Details of interest

  • Price: from 31 euros per person approximately.
  • Duration: from 1 hour and a half to 2 hours.
  • Means of transportation: on foot.

Book a gangster tour in Chicago

8. Chicago Ghost Tour

Chicago Ghost Tour| ©Eric Bartholomew
Chicago Ghost Tour| ©Eric Bartholomew

If you like mystery and ghosts don't scare you, you can take advantage of your stay in the city to take some ghost tour in Chicago. There are very interesting tour options that address these topics and satisfy the expectations of the most avid mystery seekers.

These tours are usually conducted at night to further increase the atmosphere of tension and go through the most important places in the city, known for being "haunted".

There are even tours guided by real professionals and scholars of paranormal phenomena such as Ursula Bielski, a true expert on supernatural subjects.

Keep in mind that this type of excursion is not suitable for minors or people who are easily impressed. Therefore, if you are traveling with children do not choose this type of tour, opt for one of these activities to do with children in Chicago.

Details of interest

  • Price: from 42 euros per person approximately.
  • Duration: 2 hours and a half.
  • Means of transportation: bus.

Book a ghost tour in Chicago

9. Chicago night tours

Night Sightseeing Bus| ©Alanscottwalker
Night Sightseeing Bus| ©Alanscottwalker

When you're on a trip, to truly get to know a city you must tour it at night. Chicago is no exception. You can choose from a wide variety of night tours according to your preferences.

In Chicago there are night tours by foot, by bike, by bus or also by car if you choose one of the private tours. There are also options for themed night tours such as mystery, ghost, architecture or food tours.

There are options for all tastes and budgets so you have no excuses for not touring Chicago at night. If you'd like to cruise the city's lights from the lake, you can do that too.

Details of interest

  • Price: prices vary according to the type of tour and the means of transport chosen, but you can find night tours from around 40 euros.
  • Duration: from 1 to 3 hours, depending on the option chosen.
  • Means of transport: on foot, segway, bicycle, bus, car or boat.

Book a sightseeing bus tour in Chicago

Other thematic tours that may interest you

There are not few tours offered in Chicago. Considering that we are talking about a big city with a lot to tell about its architecture, history and culture, you will be able to choose from a lot of themed tours that, thanks to the explanations of a specialized guide, you will be able to better understand everything that this incredible American metropolis has to offer. Here is a list of some other tours that may interest you:

  • Chicago art deco skyscrapers tour: from €29, an hour and a half tour of the towering skyscrapers to understand their strong art deco influence.

  • Chicago street art tour: the urban art of Wicker Park or Logan Square Chicago awaits you in this route through the coolest works of the street community. Approximately 28 euros

  • Private driving tour of Chicago this exclusive driving tour of about 3 to 4 hours is for those discerning travelers who want to tour the city comfortably with a local guide who will take them privately to see all the sights of the city. Around 480 euros with transportation from the hotel and driver.

  • Graffiti workshop in Chicago: if you are interested in urban art and want to learn how to make graffiti with this workshop you can unleash your creative side. It is not a tour as such but it is a highly recommended activity to do in Chicago. It costs about 40 euros.

How to book a tour in Chicago

Booking Online| ©Peter Olexa
Booking Online| ©Peter Olexa

The different tours around the city of Chicago can be booked online in companies specialized in selling tour packages, excursions and experiences as in our website Hellotickets.

By booking this way you ensure the availability of the tours you intend to do on the dates chosen.

It is advisable to book your tours in advance and do not wait until the last minute, because they are easily sold out.

One of the great advantages of booking tours online is that you can compare prices and also pay with credit or debit cards.

You will also have the opportunity to see the other tour options, know if there are offers available and also know the benefits of the Chicago tourist passes.

Book your Chicago Sightseeing Pass