Chicago Highlights: Story of a Gangster
4.3946 Reviews135 people have played this questYou'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!!
How many are playing?
Unlock · $9.99Staying 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
What you'll actually do
Download the Questo app and unlock the quest. Walk to Exchequer Restaurant & Pub whenever you like · no guide, no group, no time slot.
Solve 10 puzzles hidden in the streets around you. Each one you crack unlocks the next location.
Finish at Holy Name Cathedral Rectory and see where you land on the Chicago leaderboard.
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
Landmarks & Hidden Gems Included
Holy Name Cathedral Rectory
Old Chicago Water Tower District
DuSable Bridge
Tribune Tower
Ratings and Reviews
46 ratings
Renee Sandri
Dominic Brooks
Rocio
Jonathon McIlwain Sr.
Nathalie
Made by C Shiple
C Shiple created this quest · the route, the puzzles and the story are theirs.
Meet the makerThe 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.
Beat the best: Top Chicago explorers
Good to know before you play
- Not for kids
- Don’t enter the places, not part of the experience
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–$60 (€23–€50) 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–$60 (€23–€50) 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 |
Joined by 1,000,000+ explorers worldwide
Guided tour pricing: Comprehensive Economic Analysis of Guided Tour Pricing, EU and US markets, 2026. Standard 2–3 hour group walking tours.
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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.
