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: Exchequer Restaurant & Pub, 226 S Wabash Ave, Chicago, IL 60604, USA
🛡️ Free Cancellation: Cancel up to 24 hours before your planned start for a full refund.
🌐 Available In: 🇬🇧 English
Single Mission
Just looking for a single adventure?
Chicago City Pass
The complete Chicago adventure.
Annual Pass
Play any quest in 1000+ cities for the price of a dinner for two.
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
Good to know before you play
- Not for kids
- Don’t enter the places, not part of the experience
Tips & Recommendations
Wear Comfortable Shoes
You will be walking throughout the city, so comfortable footwear is essential for enjoying the experience.
Charge Your Phone
Make sure your smartphone is at least 60% charged. The quest runs through the Questo app, and you will be using it throughout.
Check the Weather
This is an outdoor activity. Bring an umbrella or sunscreen depending on the forecast.
Bring a Camera
You will discover photogenic locations and hidden gems perfect for capturing memories.
Stay Hydrated
Bring water, especially during warmer months or longer quests.
Play with Friends
While you can play solo, quests are more fun with friends or family. One ticket works for a group.
Ratings and Reviews
45 ratings
Beat the best: Top Chicago explorers
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Compare Questo vs. Guided Walking Tours
Flexibility
Regular Guided Tours
Fixed schedules & no pausing
Questo
Start, pause, and resume anytime
Privacy
Regular Guided Tours
Crowds of up to 30 strangers
Questo
Private experience for your group only
Pricing
Regular Guided Tours
$30-$40 per person
Questo
Affordable per-group pricing
Availability
Regular Guided Tours
Requires advance booking
Questo
Instant access 24/7/365
Experience
Regular Guided Tours
Passive listening to a guide
Questo
Active gamification; you solve the mystery
| 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 |
