Chicago Highlights: Story of a Gangster

4.45 (38 ratings)
Quest image more than 2
Open gallery
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!!

Availability:

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

  • During these hours
    Whole day

  • Languages
    English

Highlights

  • 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

Storyline

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

Loading...
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

10

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 play in the real-world with the ones you love

Download Questo, create an account, and find the quest you want to play.

Download on the App StoreGet it on Google Play

Ratings and Reviews

4.45

38 ratings

5 Stars
53%
4 Stars
39%
3 Stars
8%
2 Stars
0%
1 Star
0%
Reviews
Sort by

Jonathon McIlwain Sr.

16 Jun 2025
fun adventure for the family to learn more about the city

Nathalie

07 Jun 2025

FCF

07 Jun 2025

edgar mejia

06 Jul 2024

mjsbungalow

13 May 2024

How to play Questo?

  • Walk, Solve & Explore the Real World

    Download the Questo app, pick your self-guided adventure, and start exploring. Follow clues, solve puzzles, and unlock hidden stories as you discover new locations—all at your own pace.

  • Visit cities with Walking Tour Quests

    For your next trip, explore by going on a walking tour quest without a guide. Enjoy the flexibility of starting and stopping the experience whenever you want, without the fear of missing out on the best places to visit or the best stories to learn.

  • Make Your Date Unforgettable

    Turn an ordinary date into an adventure for two. Stroll through scenic streets, solve puzzles together, and share memorable moments. Perfect for couples, first dates, or even proposals.

  • Role-play in your city

    Attend a Questo Event, and immerse yourself in your favourite stories. Dress up in a costume for extra fun.

Leaderboard

FCF
3100 XP
CHRISTOPHER SURGEN
3100 XP
Judith Schultz
3100 XP

Have an unlock code?