Chicago Urban Adventures
Urban adventures that bring Chicago's secrets to life
- Work together to solve fun challenges & puzzling clues Perfectly balanced & location-based.
- Guided by clues sent to your phones Messages sent to you and your team's phones.
- Explore Chicago's historic landmarks and hidden gems Our speciality, discovering and showing off amazing places!
- Discover top-rated pubs, bars and cafes - all optional Optional breaks to catch a rest along the way.
- Compete Set the fastest time and see you ranking on your end certificate. for top spot on the Chicago leaderboard
Hunt clips...
How it works
- Choose your adventure and invite a team of 2-8 players, get competitive with multiple teams!
- Solve a trail of clues that reveal your path, sent to your phones as you hunt across the city.
- Pause at built-in break points to grab food and drinks on the way, all optional recommendations!
Don't have a great time?
Simply let us know why and we'll refund you in full.
Gift an experience
Choose from over 125 top-rated experiences across 40 cities, or choose a gift balance for ultimate flexibility. We're happy to switch should your recipient wish to change!
Chicago Experiences
Each trail takes place in a different area of the city - click each tile to learn more!

Lost in the Loop
Architectural giants and secret treasures of the North Loop… more

- Coming soon, get notified
Magnificent Mile
A magnificent mile at the heart of Chicago… more
change the date, time, number of people or game.

- Coming soon, get notified
Chicago Old Town
Hunt back in time at the 'Cabbage patch'… more
change the date, time, number of people or game.

- Coming soon, get notified
Chicago Chinatown Hunt
A hunt to hit all the senses… more
change the date, time, number of people or game.
Chicago Reviews
The great things you say about CityDays Urban Adventure Hunts

James’ Angels
We had a great time as a group of four doing the route. All four of us have lived in London in different areas, but doi…

Pip & Kate
We had a great day out. Loved the puzzles and got to see parts of London i didn’t know existed!

Fire Breathing Rubber Duckies
We had such a fantastic time on the Race Across the World Experience. From the moment it began, we felt like we were o…

Hell Nah Bros
It was good, not too difficult. Great idea for a family day out!

The Kays
Amazing would 10/10 do it again amazing to do I loved it ! 😻

CHICKENS
A really good few hours - showed us parts of Nottingham we never knew existed!

The Times
Awesome day out - saw a side I had not seen in London

Paul McCartney
Done quite a few of these now- with work and also got my family involved now- such great fun!

JS United
Excellent activity! Great questions and a way to see part of the city we never knew existed!!! Thank you 🤩

LouMo
We had a great day out in Glasgow. Learning and having fun as we went. It was a great way to see the city especially as…

Wellers & Boyd
Good fun, informative and a good family day out. Shout out to staff at viaduct tavern who took the time to show us the …

The Daring Duo
Enjoyed the adventure - well thought out. There were times we circled round but then found the correct way.

Mayfair Girls
Great walk, clues and history lesson

Woody & Ange
Great day out, this is the first time we have done an escape room. Throughly enjoyed it. Thank you for a wonderful expe…

Dreamteam
Sehr gute längere Tour die die Umgebung um Bekannte Sehenswürdigkeiten erkundet

JT’s Team
Great fun

E.U.
We loved this experience! It was challenging without being too difficult. The only downside is that you have to pass th…

Hutch
Absolutely loved taking part 'Secrets of the Squares' - our second CityDays tour and we're about to book one in Bristol…

Sherlocked doors
Had a lot of fun with our city days adventure! always fun to learn new things and solve the clues.

Mr J & The Pepperoni
Had a wonderful time exploring Brighton and cracking clues as we went!
Ready to see lots of smiling faces? Read all our customer reviews
Action-packed Urban Adventure Hunts in Chicago
How the Chicago days out work
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Discover Chicago's secret places
- Experience Chicago's unique places and share stories in independent pubs & cafes, curated for each Chicago Urban Adventure Hunt.
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Fun challenges
- Engaging puzzles and captivating stories reveal Chicago in a new light.
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Play together or competitively
- Work as a team or compete head-to-head to set the fastest time on our Chicago leaderboard.
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Fully flexible bookings
- Alter your booking freely; change the date, time, number of people or chosen Chicago Urban Adventure Hunt. Even stop and start once you've begun.
Fun activity for all groups



