Gangsters and Ghosts of Chicago: Plunging into the Dark History of the Vice City

About this activity

Audio tour
Audio tour in English
Route length: 4.5 miles
Instant confirmation
Duration 1h 30m - 2h
Audio tours on your smartphone
After purchase, you will receive the link to download the app to take this tour
Control your experience
With the in-app audio guide, you decide when to start, pause, and finish your tour
No internet is required
All audio tours and tickets can be downloaded to your device anytime

Tour preview

Hosted by Alexandra
Instant confirmation
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  • You'll receive a self-guided audio tour right after booking
  • Explore ghost and crime sites of the roaring city at your own pace with this in-app audio tour
  • Discover the most haunted sites and buildings securing tragic and mysterious stories of Chicagoans
  • Hear about rise and fall of the most infamous gangsters of all times, Al Capone and John Dillinger
  • Dive into the atmosphere of Chicago's turbulent era of the Prohibition and the Great Depression
  • Stroll along the picturesque Chicago River and learn what tragic story is covered by its waters
Spice up your visit to Chicago on this in-app audio tour through the creepiest places of the city of lights! Walk along the bubbling Chicago Loop to see the places of hangouts and crimes of cheeky bootleggers and stylish mobsters in the roaring 1920's. Hear the story of rise and fall of the most infamous gangsters of all times - Al Capone and John Dillinger. On your way, you will see such iconic sights of the city as Cloud Gate with its unusual perspective of Chicago's skyline reflected on its mirror surface. Take a selfie with the authentic Chicago Theater representing the era of swirling jazz parties and shiny speakeasies. Dark windows of ghost-haunted Congress Plaza Hotel, which inspired Stephen King's "1408" story, will surely give you goosebumps. Enjoy the skyline of Chicago Riverwalk and hear about the Eastland disaster concealed by its waters. Du Sable Bridge will give you an insight to such historical events as Great Chicago Fire and Fort Dearborn Battle, as well as to a cinematic gangster chase. Marvel at gothic architecture of the Holy Name Cathedral and find the traces of bullets in it. Then, take a short bus ride to Lincoln Park to learn the mysteries of the largest city's park. In this area, you will visit the site of spine-chilling St. Valentine Day Massacre. The tour ends at the Biograph Theater securing the story of the elusive John Dillinger. Choose to visit restaurants and attractions to enforce your Chicago gangsters and ghosts experience.

What's included

  • Downloadable multimedia audio tour on WeGoTrip app
  • Detailed route from stop to stop with live GPS map on your smartphone
  • Recommendations for museums and further ghosts and gangsters experience
  • Self-guided audio tour for your smartphone on the WeGoTrip app
  • Earphones not included — bring your own
  • Cash or transport cards to take a bus or a train
  • Earphones and smartphone are not included – bring your own
  • In-person tour guide

Places you will visit

The route of the tour goes within circle
Blackstone Hotel
East Balbo Drive, Lobby Entrance On
Biograph Theater
North Lincoln Avenue, 2433
Download the app and the digital audio tour on your smartphone before the visit. You will find recommendations on how to get to the staring point in the first step of the tour. If you have any questions or need any assistance, please email us at
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Cancellation policies vary according to activity type. Please check the conditions of your required activity Self-guided audio tour.
Hi! I'm a traveler, a guide, and a travel content creator 🌍 With my audio tours, I share my passion to my beloved places, cities, and museums! Travel with me through my planned routes and amazing stories!

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