Chicago Highlights: Story of a Gangster

4.48 (31 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!!


  • Can be played on
    Monday, Tuesday, Wednesday, Thursday, Friday, Saturday, Sunday

  • During these hours
    Whole day

  • Languages

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  • 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.

 ince 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.

Experience's 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

Places you will visit


It will take you

57-87 mins

You will walk

5250 steps

Total distance

4 km

  • Not for kids
  • Don’t enter the places, not part of the experience
People exploring Glasgow with Questo

Get the Questo app and you’re all set

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

Download on the App StoreGet it on Google Play

Ratings and Reviews


31 ratings

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edgar mejia

06 Jul 2024


13 May 2024


06 May 2024


02 Mar 2024


02 Jan 2024
A really excellent story with lovely slices of Chicago history as well - a good, fun walk with great writing! Thanks for a fun new way to explore downtown Chicago.

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3100 XP
Judith Schultz
3100 XP
3100 XP