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Chicago Gangsters (GAME IN TEST MODE)

An historic walk that tells the story of Chicago's emergence from the ashes of the Great Chicago Fire.  Your stroll takes you from the heart of downtown north across the river.  You'll see world famous landmarks while learning answers to the city's most compelling questions:  Where was the world's first skyscraper?  Why are there two Wacker Drives stacked on top of one another?  What's the real reason it's called "The Windy City"?  And lest we forget -- GANGTERS!!
No booking needed. Just download the app, add it to your quests and start playing.
  • Not for kids
  • Don’t enter the places, not part of the experience

Places you will visit


It will take you

57-87 mins

You will walk

5250 steps

Total distance

4 km


  • Take in the most interesting sights of the biggest city in America's heartland

  • Hear the story of the most infamous of Chicago sons, Al Capone

  • Starting in the the city's famed Loop, you'll visit iconic sights like the Tribune Tower and the Chicago River

  • Take in the Magnificent Mile and end up in a place where you can still see bullet holes from the city's violent past


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It’s 1930. Things been tough for your family for the last year, just as it has been for most Americans during the Great Depression. Since your father died unexpectedly, it’s up to you to support your family. You heard that Al Capone’s criminal “business” is always looking for help. 
You decide to give it a shot.

Game route

Starting point Exchequer Restaurant & Pub
226 S Wabash Ave, Chicago, IL 60604, USA
Finish point Holy Name Cathedral Rectory
730 N Wabash Ave, Chicago, IL 60611, USA



2 reviews

5 Stars
4 Stars
3 Stars
2 Stars
1 Star
All reviews (2)

Jennifer Walston

Mar 2022
we had fun with this! would definitely do another.

Lena Walston

Mar 2022


Lena Walston
2537 XP
Jennifer Walston
1926 XP
100 XP

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Get the app and you're all set

Download it, choose your route and just walk to the starting point.

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How does a
game look like?

  • Discover new places

    As you walk and tour around the city, you will visit new cool places.

  • Solve puzzles, crack riddles

    You will test your wits and exploring abilities with fun challenges.

  • Learn fun history

    Each place comes with its own bit of history that you'll discover as you walk.

  • Role-play

    Put yourself in the shoes of a famous fictional character and play out their story.