Best 12 Tours And Excursions In Chicago! - Updated 2024

Contributing Writer
| 5 min read

Chicago is one of the most well-known cities in the US with its famous hotels and marvellous wonders. When you think about Chicago, the first thing that comes to mind is pizza! I agree, pizza is love, but this magnificent city also gives us some amazing adventures to create beautiful memories. From the stunning architectural wonders such as the Sears (now Willis) Tower and The Bean to the eclectic arts and culture scene, there are so many amazing places to uncover. However, it’s hard to decide where to go, what to see, what to eat; it’s a confusing mess! If you have plans on booking your stay in a fancy rental or a budget hotel, consider checking out these fun-filled trips that give you all the best the windy city has to offer. Don’t know what to do? Here are our best tours and excursions in Chicago worth checking out!

1. Gangsters and Ghosts Tour (from USD 35.0)

Chicago once used to be a hotspot for some of America’s most intimidating mobs and legendary gangsters. If you’re up to uncover what history unfolds within the city streets - and like getting spooked up - then this walking tour is worth booking your slots for. For about two hours, a historian will take you through the places mobsters often frequented.

Take a stroll through the Chicago Loop, which was once littered with prohibition-era speakeasies and bootleggers and has now become a lively downtown stop. There are also some significant stops throughout the tour, including the Palmer House and Congress Plaza hotels. Urban legend says that those historic hotels are haunted. Al Capone’s HQ office used to stand in Congress Plaza, so there’s a good chance that you might spot his ghost roaming around the hallways.

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Chicago: Gangsters and Ghosts Tour Walking Tour

Duration: 2 hours

6067 reviews

2. Mob and Crime Bus Tour (from USD 49.0)

best tours in chicago | mob and crime bus tour

True crime enthusiasts will certainly have a memorable time taking a tour across Chicago by bus as they explore the windy city’s dark side. Historic crime scenes, significant landmarks, and interactive activities await in the Mob and Crime Bus Tour, where tourists can get to learn in-depth about how America’s most notorious gangsters schemed their way into Chi-town.

A highlight of this tour is the trip to the site where the infamous St. Valentine’s Day massacre took place, while the building that housed the former criminal courthouse has stunning exteriors that are a sight to behold. Not only will you be taking pictures, immersing in videos, and participating in quizzes. You’ll also get to trek a path in the shoes of the bank robber John Dillinger before he met his tragic fate.

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Chicago: Mob and Crime Bus Tour

Duration: 1.5 hour

608 reviews

3. Tommy Gun’s Garage Dinner and Show

#TBT Da old joint on State St. Who visited us at that location??

Posted by Tommy Gun's Garage on Thursday, 22 June 2017

Tommy Gun's #matinee crazy things happen. #halloweenforchristmas #achristmasstory #pinkbunnycostume #icantputmyarmsdown #auntclara #daddysgonnakillralphie #speakeasy

Posted by Tommy Gun's Garage on Wednesday, 7 December 2016

Walk into the era of mobsters and rival gangs. Tommy Gun’s Garage Show brings a whole new experience to the table. This dinner theatre offers interactive, uninterrupted fun to all ages. Have a delicious sit down dinner with a musical comedy as an accompaniment. The roaring twenties décor, jazz music, and flappers add to the unique experience. Enjoy the cultural shock with the best desserts in Chicago. Join in the fun of non-stop comedy, dancing, singing, and be prepared to be interviewed by the ‘cops’. The best part is, you cannot enter without ‘da password’!

Tommy Gun’s Garage Dinner and Show

Address: 2114 S Wabash Ave, Chicago, IL 60616, USA

Website: Tommy Gun’s Garage Dinner and Show

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4. Frank Lloyd Wright Tour

Emil Bach House
Source: Photo by Wikimedia Commons user JeremyA used under CC BY-SA 2.5

Frank Lloyd Wright, a renowned architect, believed in a philosophy he called ‘Organic Architecture.’ This tour will take you to the heart of Wright’s unique work. Visit Frank Lloyd Wright’s home and studio, where the first of his ideas came to be. Bask in the brightly lit, brilliantly structured court of The Rookery, a Chicago landmark. Explore the futuristic, fireproof Bach House. Learn about the life and work of a man who contributed to and influenced modern architecture.

Frank Lloyd Wright Tour

Address: The Rookery, 209 S. LaSalle Street, Suite 118, Chicago, IL 60604

Website: Frank Lloyd Wright Tour

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5. History on Tap

No matter where we travel, we always make sure to carve out some time to dig into some local beer history. In Milwaukee...

Posted by History On Tap on Friday, 21 April 2017

The 2016 History On Tap International drinking and learning excursion has begun!

Posted by History On Tap on Saturday, 24 September 2016

What is the best way to get a history lesson, you ask? I say, in a pub, with a beer in your hand. History on Tap is all about Chicago and its drinking culture. Head over to the Chicago Brewseum, the first beer museum in Chicago with recorded history of one of the oldest beverages in the world. Listen to the story of Beer and how it incorporated itself into Chicago’s daily life. There is no better way to spend a holiday than in the Brewseum!

History on Tap

Address: 928 W. Roscoe St., Chicago, IL 60657

Website: History on Tap

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6. Devil in the White City Tour

Posted by Paul Fein on Sunday, 7 October 2012

Looking for Dr. Holmes stalking the Worlds Fair.

Posted by Michael Horsting on Saturday, 10 September 2016

‘Devil in the White City,’ a book by Erik Larson, explores the true events that happened in Chicago in 1893. It is a tale about Daniel H. Burnham, a leading architect behind the 1893 World Fair in Chicago and Dr. H. H. Holmes, a con artist and a serial killer. At first this might seem like a creepy tour; what’s there to see about a serial killer, skeletons? Nah! This tour explores the intriguing story of these two characters. The bus tour will take you across the town, exploring various historical buildings where the events in 1893 took place. It’s fascinating, like going back in time!

Devil in the White City Tour

Address: Chicago Architecture Foundation, 224 S. Michigan Ave., Chicago, IL 60604

Website: Devil in the White City Tour

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7. Urban Kayaks Tour

Every summer has a story, let us be a part of yours! ☀️ Come visit us down on the #chicagoriverwalk for a great summer adventure🚣

Posted by Urban Kayaks on Friday, 14 July 2017

Looking for the best spot to watch Navy Pier's amazing summer fireworks show? It's here! Come grab a paddle, and join us...

Posted by Urban Kayaks on Wednesday, 12 July 2017

For those early birds who love water sports, there is a wide array of kayaking tours on the Chicago River’s main branch. Float along the river on this tour to get to know Chicago inside out. The excursion is 1.5 hours long with rest stops where your guide will tell you about the rich history of the city skyline’s architecture. If you are there with your significant other, you might want to opt for the Ultimate Fireworks Outing for a romantic evening on the river.

Urban Kayaks Tour

Address: 1. Chicago Riverwalk, 435 E. Chicago Riverwalk, Chicago, IL 60601. 2. Ogden Slip, 465 N McClurg Ct, Chicago, IL 60611

Website: Urban Kayaks Tour

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8. Chicago Greeter tours

Posted by Choose Chicago on Wednesday, 11 June 2014

Tom Norton with guests from France

Posted by Choose Chicago on Wednesday, 25 May 2016

You are new in town and lost in the maze of the big city, what do you do? Ask a local of course! Chicago greeters take this one step ahead. An expert local will take you on a tour of all the insider spots for 2-4 hours. These passionate locals work as volunteers so the tour is free of cost! If you want to take part of a sightseeing trip in Chicago, it’s best to book it 10 days prior. But what about those forgetful birds? No worries, they’ve got Instagreeters! They are guides who swoop in at the last minute and save the day. Your designated instagreeter will take you Downtown for an hour long walk so you can enjoy all the temptations.

Chicago Greeters

Address: 72 E Randolph St, Chicago, IL 60601, USA

Website: Chicago Greeters

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9. Chicago Pizza Tour (from USD 89.0)

Chicago and pizza go hand in hand. Enjoy the city’s pizza culture with this amazing tour. Learn about the top notch ingredients used to make the best cheesy delicacy. Get educated on the pizza making process. Understand the secret to that magical buttery crust! Go to the favorite local restaurants and learn the history of pizza with a delicious slice in front of you. This 3.5 hour tour takes you through the best restaurants to sample different types of toppings and pizza styles.

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Chicago Neighborhoods Guided Pizza Bus Tour

Duration: 3 hours 30 minutes

383 reviews

10. Chicago Prohibition Tour (from USD 55.0)

The alcohol prohibition in United States lasted from 1920 till 1933. The Chicago Prohibition Tour takes us right through history. The tour lasts 2.5 hours, educating you on the history of the prohibition era. This is one tour where you’ll get to drink booze that represents the prohibition years. Take a sip of this rich history and learn all about the Jazz age to influences in the Sexual Revolution. Though you must be at least 21 years of age to enjoy this ride!

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Chicago Adults-Only Historic Bar and Speakeasy Tour

Duration: 3 hours 30 minutes

10 reviews

11. Chicago Film Tour (from USD 30.0)

Whether you've done it before, or have guests or relatives who haven't, come celebrate the traditional last weekend of...

Posted by Chicago Film Tour on Friday, 4 September 2015

CFT Guide Patrick McDonald does his best Elwood at the Wrigley Field movie night showing the 'Blues Brothers'

Posted by Chicago Film Tour on Saturday, 7 July 2012

Chicago has been a backdrop to many famous films, ‘The Dark Knight’, ‘North by Northwest,’ and many more. Embark on a journey which takes you to various spots where the famous scenes were filmed. Over 80 movies are featured in these tours. Learn the fun facts about the city’s incredible film history.

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Chicago Film Tour

Duration: 2 hours

10 reviews

12. Chicago by Night Helicopter Tour (from USD 179.0)

Chicago Night Skyline
Source: Photo by user Ben Grey used under CC BY-SA 2.0

Get on the best ride in Chicago and enjoy the thrill! Need a change of perspective? Reach the clouds, sit back and enjoy an aerial view of the city. Look at the crawling traffic on Chicago roads and pedestrians busy as bees. Enjoy the evening sunset or the nightlife of the city from the heavens. Go up there with your special someone and enjoy the firework display; what a magnificent view!

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Chicago by Night Helicopter Tour

Duration: 30 minutes

10 reviews

A tourist heaven

Chi-town can be called a tourist heaven since there are so many things to do and so much to see! Having someone to help you find the itinerary that interests you might be hard sometimes, so try some of Chicago’s finest tours that are best suited for different people and their interests. Have you enjoyed our little list? Tell us all about it!

Frequently asked questions about the best tours and excursions in Chicago

  • Which are the best tours in Chicago for groups?

    If you happen to bring your posse of friends to the windy city, it’s a must to take them on exciting excursions such as the Gangsters and Ghosts tour, History on Tap, the Urban Kayaks tours, and the Chicago pizza bus tour.

  • What tours in Chicago are good for avoiding crowds?

    If you want to explore Chicago whilst avoiding large crowds, activities such as the Frank Lloyd Wright tour, the Devil in the White City bus tour, and the Urban Kayaks tour are great options. The Chicago Greeter tour is also an ideal choice, but the experience is best enjoyed if you book a slot earlier by 10 days.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Kasturi is an avid reader and traveler. Based in India, she works as a freelance travel writer. On days she's not writing, she goes hiking with her dogs. She likes to travel to places where she can...Read more

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