Team vs team
Use your own phones and join a team. Any teammate’s answer advances everyone. Beat the other teams on the leaderboard.
Outdoor adventure for kidsFamilies with kids
Chicago Highlights: Story of a Gangster
4.39Player ratingBIG ADVENTURES FOR CURIOUS MINDS
Play at your pace · usually 72 min 4 km Chicago App-guided
Play in
English
Little explorers. Big discoveries.
An adventure to share.
Follow the clues, swap ideas and discover what your family can solve together. Let curious minds lead the way, with a grown-up along for the adventure.
- Explore togetherA shared outdoor adventure
- Bring your curiosityLook closely. Think together.
- Plan your family outingCheck the route and practical details
YOUR FAMILY’S NEXT ADVENTURE
A little curiosity goes a long way.
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!!
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!!
What makes this quest special
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
From people who played this quest
Good times. In their words.
4.39 / 5
46 player ratings
Selected player reviews. Original words and ratings.
Most relevant starts with detailed five-star reviews. All ratings remain available.
From your phone to the streets
A walk that turns into an adventure.
- 1
Open the app. You’re on your way.
Choose your pass, then open your quest in the Questo app. It guides you from the starting point.
- 2
Get outside. Follow your curiosity.
Discover real places and their stories on foot. Stop for a coffee or a photo, then pick up where you left off.
- 3
Crack a clue. Share a little victory.
Solve clues together and celebrate every discovery, with an adult helping along the way.
CHOOSE YOUR PASS
How many are playing?
Get this questNo booking slot · play any dayFull refund until you start playing
BRING YOUR WHOLE GROUP
One city. Rival teams. Great stories together.
A school trip, a team day or friends out together. Turn your next outing into a little friendly competition.
Everyone for themselves
One player per phone. Solve clues on your own and race for the top spot on the final leaderboard.
Can a team share one phone?
Yes. Play together on one phone per team, or use your own phones and join the same team in the app. We recommend your own phones so everyone can take part.
Your walk, at a glance
Chicago
A · Start
226 S Wabash Ave, Chicago, IL 60604, USA
B · Finish
730 N Wabash Ave, Chicago, IL 60611, USA
Start and finish only. Discover the stops as you play.
Along the way
Landmarks & Hidden Gems Included
The people behind the adventure
Created by C Shiple.
A route that brings places and playful storytelling together.
Made by C ShipleWHAT MAKES A QUEST DIFFERENT
Your adventure, with a playful twist.
1 / 4
Experience
- This quest
- Discover places through stories and clues in the app
- Guided walking tour
- Hear stories and ask a guide questions
2 / 4
Pace
- This quest
- Pause for a photo, a café or a longer look
- Guided walking tour
- Usually follows the guide’s schedule
3 / 4
Company
- This quest
- Explore with your own people or on your own
- Guided walking tour
- Private and shared group tours are available
4 / 4
Guidance
- This quest
- Directions and challenges in the Questo app
- Guided walking tour
- Live interpretation from a guide
Features and terms vary by experience. Check the details before booking.
Good to know before you play
- Not for kids
- Don’t enter the places, not part of the experience
A little clarity before you go
Frequently asked questions
Is Chicago Highlights: Story of a Gangster self-guided?
Yes. The Questo app guides you between locations without a tour guide or fixed departure. Start when it suits you and pause if needed.
Where does Chicago Highlights: Story of a Gangster start and finish?
It starts at Exchequer Restaurant & Pub, 226 S Wabash Ave, Chicago, IL 60604, USA and finishes at Holy Name Cathedral Rectory, 730 N Wabash Ave, Chicago, IL 60611, USA. The route is approximately 4 km and includes 10 location-based puzzles.
How many accesses does our group need?
This classic quest sells access per device and player. Each person who wants to solve clues on their own phone needs their own access.
What language is Chicago Highlights: Story of a Gangster available in?
It is currently available to play in English.
Keep exploring
Every quest. One year.
Explore the annual passGive them a story
A day out, gifted.
Explore Questo giftsKeep exploring Chicago
More adventures in Chicago
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.
