Chicago Highlights: Story of a Gangster

4.5 (10 ratings)
Quest image more than 2

A 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 – GANGSTERS!!

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  • 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

3940 steps

Total distance

3 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


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
People exploring Glasgow with Questo

Get the app and you're all set

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

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Get it on Google Play

Ratings and Reviews


10 ratings

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Jessica Jensen-Fisher

12 Sep 2022

Abraham Adberstein

23 Jul 2022

Adam Moldover

12 Jul 2022

Anthony D

06 Jul 2022

William Shiple

15 Jun 2022
cool facts and fun story

What 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.


Colin Vick
3100 XP
Anthony D
3070 XP
Gracelyn Pavy
2999 XP