Chicago Highlights: Story of a Gangster
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!!
Staying a few days in Chicago? All 8 Chicago quests for $39.99 — pays for itself by quest #5. See the Exploration Pass →
Places you will visit
10
It will take you
57-87 mins
You will walk
5250 steps
Total distance
4 km
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
Bring your crew
Race to the finish.
Everyone plays on their own phone — race solo, as a couple, or with a crew of any size. First to solve every clue takes the crown.
Adventure
Your pace, no timer
Escape
Beat the clock
Plays offline at your own pace — live group races need a connection.
Final leaderboard
Landmarks & Hidden Gems Included
Holy Name Cathedral Rectory
Old Chicago Water Tower District
DuSable Bridge
Tribune Tower
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.
FAMILY ACTIVITY IN CHICAGO
A kid-friendly outdoor mission in Chicago
Chicago Highlights: Story of a Gangster is for families who want an active outdoor alternative to another screen-heavy or venue-only outing in Chicago. Children follow a story, solve clues and turn the city route into part of the game.
The route starts at Exchequer Restaurant & Pub and finishes at Holy Name Cathedral Rectory over 4 km, with 10 challenge locations. Typical duration: 72 min; 4 km walking route; 10 challenge locations
Choose this when you want a flexible family mission outdoors. Choose a cinema, zoo or indoor attraction when a fixed venue and facilities matter more. Playable languages: English.
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
Quests are more fun with friends or family. Each player who wants to play on their own phone needs their own access.
Ratings and Reviews
46 ratings
Renee Sandri
Dominic Brooks
Rocio
Jonathon McIlwain Sr.
Nathalie
Beat the best: Top Chicago explorers
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Frequently asked questions
Is Chicago Highlights: Story of a Gangster self-guided?
Where does Chicago Highlights: Story of a Gangster start and finish?
How many accesses does our group need?
What language is Chicago Highlights: Story of a Gangster available in?
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
Transparent pricing shown before checkout
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 | Transparent pricing shown before checkout |
| Availability | Requires advance booking | Instant access 24/7/365 |
| Experience | Passive listening to a guide | Active gamification; you solve the mystery |
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