It’s hard to image the largest city in the Midwest as being nothing more than an outpost town in the past, but this is exactly where Chicago can trace its beginnings. It wasn’t until its waterways were maximized and canals and sewers built that its growth boomed, and it even served at some point as a model that other American cities followed in terms of using engineering to spur their own success. As these developments were happening, the city also began welcoming migrants, which is why the city has become a melting pot of cultures. Get to know the secrets behind the Windy City’s success by signing up for the best history tours in Chicago, Illinois.
1. Get to know the ghosts and gangsters of Chicago (from USD 35.0)
Want to go ghost hunting in Chicago but also want to learn about the true-crime stories in the city? Why choose from when you can join a tour that combines the two? This two-hour tour takes you through the streets of Chicago, where you get to learn about the crimes and creepy stories that surround the city. Among the characters that you will get to meet during the tour is the infamous Al Capone. You’ll also get a better idea of what life was like in Chicago during the Prohibition era.
Gangsters and Ghosts Tours
Duration: 2 hours
2. Discover the secrets behind Chicago's architecture (from USD 29.0)
This two-hour tour will allow you to see the city through the eyes of a local. The host brings her guests to the most popular locations around Chicago and shares about the city’s sights and trivia about the city itself (do you know why Chicago is called the Windy City?). You’ll also get to learn about key moments in Chicago’s past, including its history with gangsters, speakeasies, and the Prohibition era. You will even get to taste a Chicago snack along the way. Be sure to wear comfortable clothes and shoes, because this tour will require a lot of walking.
All-Weather Architecture & History Trek
Duration: 2 hours
3. Discover the secrets of Hyde Park (from USD 20.0)
Did you know that Hyde Park has a slice of history? Besides being one of, if not the most picturesque neighborhoods in the city, it also holds some secrets which, when revealed, will allow you to get better acquainted with Chicago. This tour takes guests to various landmarks and attractions in the area, including a UNESCO World Heritage Site, and reveals some juicy stories about the city, including where secret government programs were held.
Discover historic Hyde Park, Chicago
Duration: 2 hours
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4. Take a walking audio tour of Chicago's Gold Coast (from USD 5.0)
Travelers who aren’t fans of joining group tours and want to explore things at their own pace will want to check out this package. This audio tour allows you to take a closer look at the Gold coast, from the original Playboy Mansion to the oldest piano bar in Chicago. The audio syncs with your smartphone’s GPS, so you can be sure that what you’ll be hearing are the details on what you are actually seeing. The beauty of this tour is you can take time to absorb what’s around you or breeze through it: the choice is yours.
Chicago: Gold Coast Self-Guided Smartphone Audio Walking Tour
Duration: 50 minutes
5. Check out Chicago's dark history (from USD 46.0)
This tour gives its guests an insight into the dark history of Chicago. Conducted primarily on coach, travelers will be able to explore the places where the likes of Al Capone, John Dillinger, and Hymie Weiss spent their time while in the city and where their most notorious crimes were committed.
Chicago Criminals, Mobsters and Gangsters Bus History Tour
Duration: 90 to 120 minutes
6. Explore the architectural treasures of Chicago (from USD 30.0)
Chicago is known for its fantastic architecture, and this tour allows you to have an in-depth look at the history of its most famous buildings. Besides sharing with you the stories behind these structures, the host will also talk about interesting things to look out for are as you proceed with this tour. Because the buildings are presented chronologically, you will be able to imagine how the city expanded over the years.
Chicago Walking Tour: A Walk Through Time
Duration: 1 hour 30 minutes
7. Explore the historic places of South Chicago (from USD 55.0)
If you have two hours to spare, consider joining this tour, which combines getting around via a trolley and walking. The guide takes you to the historic attractions in South Chicago, including Grant Park, Buckingham Fountain, and the house of Barack Obama, the former president of America. The activity culminates at the 360 Chicago Observation Deck, where you can enjoy views overlooking the city from 1,500 ft (457 m) off the ground.
Historic Chicago South Side Tour and 360 CHICAGO Observation Deck
Duration: 2 hours
8. Take a deep dive into Chinatown's history and culture (from USD 20.0)
This is more than just a sightseeing tour. Besides bringing you to Chinatown’s famous landmarks such as the Nine Dragon Wall, the Buddhist Temple, and the Chinese Zodiac Park and giving you some information about these sites, this activity also allows you to have a better understanding of its culture. You will even get to pick up some tips on how to order Chinese food and get an introduction on Chinese traditional medicine.
Chicago Chinatown History & Culture Tour
Duration: 1 hour 30 minutes
9. Go on a speakeasy tour and try cocktails from the '20s (from USD 55.0)
Ever wondered why the Prohibition-era came to be and how people got around the alcohol ban? If so, this activity is for you. This adults-only tour takes guests to four bars that have been around since that era. The guide will give information about the world of the speakeasies and how these are tied to the lives of the gangsters from the ‘20s, including Al Capone. Cap the day with cocktails and signature drinks from that era.
Chicago Adults-Only Historic Bar and Speakeasy Tour
Duration: 3 hours 30 minutes
10. Take a closer look at the 19th-century Auditorium Theatre (from USD 12.0)
The Auditorium Theatre is a source of pride and joy of Chicago. Recognized as a National Historic Landmark, this 126-year-old venue has hosted more than its fair share of concerts, plays, and other events, but the structure itself is worth a visit. This tour will allow you to take a closer look at the magnificence of the theatre, from its 24-karat gold-leafed ceiling arches to its gorgeous wall mosaics. The host will also walk you through some of the most famous performances that have been held at this venue.
Auditorium Theatre Historic Tour
Duration: 1 hour
Uncover Chicago's secrets
They say that the only way for you to know someone is to understand his/her past. The same can be said for places - by learning about what the Windy City went through, you will also be able to have a deeper appreciation and understanding of how it evolved to its current state. While it’s fun to marvel at the city’s skyscrapers, do take the time to learn about its history so you can get to know Chicago better.
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