Chicago Highlights: Story of a Gangster
🔒 Instant Access: Book now and start immediately. No need to wait for a guide.
⏱️ Total Flexibility: Start, pause, and resume whenever you want.
🧩 Gamified Discovery: Solve 10 location-based puzzles to unlock hidden stories and secret spots.
📍 Starting Point: Place des Abbesses, Montmartre.
🛡️ Free Cancellation: Cancel up to 24 hours before your planned start for a full refund.
🌐 Available In: 🇬🇧 English
Places you will visit
10
It will take you
57-87 mins
You will walk
5250 steps
Total distance
4 km
Route you will explore
Starting point Exchequer Restaurant & Pub
226 S Wabash Ave, Chicago, IL 60604, USAFinish point Holy Name Cathedral Rectory
730 N Wabash Ave, Chicago, IL 60611, USAAbout this quest
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!!
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
The mission: Your story in Chicago
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.
Landmarks & Hidden Gems Included
Holy Name Cathedral Rectory
Old Chicago Water Tower District
DuSable Bridge
Tribune Tower
- Not for kids
- Don’t enter the places, not part of the experience
Ratings and Reviews
45 ratings
Beat the best: Top Chicago explorers
Compare Questo vs. Guided Walking Tours
| Feature | Regular Guided Tours | Questo |
|---|---|---|
| Flexibility | Fixed schedules & no pausing | Start, pause, and resume anytime |
| Privacy | Crowds of up to 30 strangers | Private experience for your group only |
| Pricing | $30-$40 per person | Affordable per-group pricing |
| Availability | Requires advance booking | Instant access 24/7/365 |
| Experience | Passive listening to a guide | Active gamification; you solve the mystery |
