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 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 hub for its culture, cuisine and entertainment activities. If you travel there, 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're looking to experience Chicago's architecture, art, food and mysteries or you prefer to discover Chicago's music shows and nightlife, this article provides a guide to the best tours of the city to help you organise 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.

As a very cosmopolitan city, the cuisine of this region is characterised by its roots in different cultures. Traditional dishes draw inspiration from as far afield as Europe and Asia, so Chicago's food is rich in both ingredients and flavours.

What to try on these tours

On food tours of Chicago you can experience the city's iconic culinary 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.

On Chicago food tours, you'll also get a taste of Chicago's famous pizza. Be warned that it is quite different from what you eat in Europe and I must admit that I was hesitant to try it at first, but after I did, I really liked it.

The Chicago style pizza or Deep Dish pizza is characterised by its thick dough and the shape of a dish in which the different ingredients (sauce, cheese, salami, etc.) are placed, making it more similar to a stuffed pizza than a traditional Italian style pizza.

Chicago's craft beer is also renowned for its quality and unmistakable flavour. You'll also get a taste of it on these comprehensive food tours of the city.

Finally, if you're looking for a local dessert, donuts are the city's signature treat.

Interesting details

  • Price: from approximately 40 euros per person.

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

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

Book a food tour of Chicago

2. Chicago Segway Tours

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, as there are companies specialised in providing visitors with tours on this increasingly popular means of transport. Segway tours have become popular in several cities around the world thanks to their practicality and economy.

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 kilometres 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 tours.

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

The guides on these tours have the certifications required by city law, which gives you added safety.

You can choose between daytime tours, visiting the city's most famous landmarks such as Grant Park and Soldier Field, or a nighttime tour of the city's mysterious and haunted sites.

Interesting details

  • Price: from 73 euros per person.

  • Duration: about 2 hours.

  • Means of transport: Segway.

Book your Segway tour of 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 go deeper into the places I find most interesting.

The Chicago sightseeing buses pass by all the city's sights and you can also use them as a quick way of getting from one place to another.

The value for money on the sightseeing bus tickets is very good if you take into account that the stops are free and you can get on as many times as you want during the validity of the pass you choose.

They also offer audio guides so you don't miss out on the details of the tour. These are in several languages, including Spanish, and are an excellent way to learn interesting facts about the city's main attractions, which will help you choose which ones are worth visiting later with more time.

Interesting details

  • Price: from 45 euros per person.

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

  • Means of transport: bus.

Book the Chicago sightseeing bus

4. Chicago Cruises

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

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

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

Sailing on Lake Michigan is something you can't 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 big waves at some times of the year, especially in winter and autumn, so it seems that you are sailing on the open sea.

Interesting details

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

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

  • 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 for a treat with the wide range of bike tours available in Chicago.

While cycling you can get to know various highlights such as the skyscrapers in Streetville or Lincoln Park and the surrounding area 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 tour (bike and helmet).

Please note that on this type of tour, as with Segway tours, you have the advantage of covering longer distances and avoiding traffic problems.

Interesting details

  • Price: from 52 euros per person approximately.

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

  • Means of transport: bicycle.

Book your bike tour of Chicago

6. Chicago Architecture Tours

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

Chicago's buildings are impressive, not for nothing is it known as "the city of architecture". In the city, old buildings and art deco buildings coexist with huge skyscrapers, giving a very special attraction to the different neighbourhoods, which does not go unnoticed by architecture enthusiasts or the general public.

There are several tour options that take in the most architecturally significant sites and are an excellent opportunity to get to know the city through the history told by its buildings.

By taking a guided tour of the best of Chicago's architecture you will learn why Chicago's building features 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.

Interesting details

  • Price: from 27 euros per person.
  • Duration: about one and a half hours.
  • 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 immortalised in series and films.

If you want to learn about the history of the mafia and the city's illustrious criminals, you can do so on tours specialising in these subjects, with guides who will tell you all about the history and take you to the places linked to the most famous gangsters.

Some of these tours take place at 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 approximately 31 euros per person.
  • Duration: 1.5 to 2 hours.
  • Means of transport: 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 go on a ghost tour in Chicago. There are some 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 add to the atmosphere of tension and take in the most important places in the city that are known to be "haunted".

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

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

Interesting details

  • Price: from 42 euros per person approximately.
  • Duration: 2 hours and a half.
  • Means of transport: 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 really get to know a city, you have to tour it at night. Chicago is no exception. You can choose from a wide variety of night tours to suit your preferences.

In Chicago there are night tours by foot, by bike, by bus or even 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 to suit all tastes and budgets so you have no excuse for not touring Chicago at night. If you'd like to cruise the city's lights from the lake, you can do that too.

Interesting details

  • 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: 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 themed tours you may be interested in

There are more than a 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 among a lot of thematic tours that, thanks to the explanations of a specialised guide, you will be able to better understand everything that this incredible American metropolis has to offer you. Here is a list of some of the other tours you may be interested in:

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

  • Chicago Street Art Tour: The street art of Wicker Park or Logan Square Chicago awaits you on this tour of the coolest works of the street community. Approximately 28 euros

  • Private Driving Tour of Chicago - this exclusive 3 to 4 hour driving tour is for the discerning traveller who wants to tour the city in comfort with a local guide who will take you privately to all the sights of the city. Around 480 euros with hotel pick-up and driver.

  • Graffiti workshop in Chicago: if you are interested in urban art and want to learn how to do graffiti, this workshop will allow you to 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 specialised in the sale of tour packages, excursions and experiences such as our website Hellotickets.

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

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 sightseeing passes.

Book your Chicago Sightseeing Pass