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Chicago Outdoor Escape Room Games

  • 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 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
Talk to us about team building options

Next Steps

1. Select your game, pick a trail of your choice and receive your welcome email.
2. Rally your team and enter a team name and phone number(s) into the system.
3. Receive your welcome text, then head to the start location on a day and time of your choice.
4. Text START to receive the first in a series of cryptic directions. Solve the puzzles to unravel your mystery.
5. Discover unique places, the secret and hidden of your city - and great independant pubs/cafes!
Full money back guarantee

Don't have a great time?
Simply let us know why and we'll refund you in full.

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Action-packed Chicago escape rooms in Chicago

How the Chicago days out work

Discover Chicago's secret places

Experience Chicago's unique places and share stories in independent pubs & cafes, curated for each Chicago Chicago escape room.

Fun challenges

Engaging puzzles and captivating stories reveal Chicago in a new light.

Play together or competitively

Work as a team or compete head-to-head to set the fastest time on our Chicago leaderboard.

Fully flexible bookings

Alter your booking freely; change the date, time, number of people or chosen Chicago Chicago escape room. Even stop and start once you've begun.

Fun activity for all groups

Corporate Treasure Hunts
Work together with friends & family
corporate treasure hunts
Relaxed Chicago date treasure hunts
Corporate Treasure Hunts
Chicago competitive team building treasure hunts
corporate treasure hunts
Fun-filled Chicago hen-do treasure hunts

Chicago escape room Reviews

The great things our customers have to say about CityDays Chicago escape rooms

RuddRobins Chicago escape room


Wonderful way to explore, Nottingham next!

Mayo for Sam Chicago escape room

Mayo for Sam

Great afternoon of puzzles and fun.Everyone enjoyed and even those of us who know London still discovered new things & …

You got snacks? Chicago escape room

You got snacks?

This is the second one of these we have done, we love them. Great day out and takes you places you've not been before. …

Bubbles Chicago escape room


We had a great time. Got stuck on one clue when it said look right not left, but worked it out in the end. We took a fe…

Definitely Maybe Chicago escape room

Definitely Maybe

Excellent experience. Really quick messaging and challenging but fun clues

Dally101 Chicago escape room


Myself and my partner really enjoyed this activity. I'm from Scotland and he is from outer London and both found it a g…

Team London birthdays Chicago escape room

Team London birthdays

We had a really great time! Really made my birthday!

TJT Chicago escape room


Such a unique and fun experience! It really allows you to see parts of the city that you wouldn’t necessarily visit! In…

Ru and Coel Chicago escape room

Ru and Coel

It was amazing getting to tour all the little details of Sydney while having an underlying story and puzzles to solve! …

Princess Squeak & the Silly Goose Chicago escape room

Princess Squeak & the Silly Goose

Such good fun, clever clues, and the trail took us to see parts of York we have never seen before! Loved it!

The Band on Tour Chicago escape room

The Band on Tour

A really fun day out. Got to see lots of the city and learn some interesting facts too!

Blakemores on Tour Chicago escape room

Blakemores on Tour

Excellent way to see the city

Joe’s adventure squad Chicago escape room

Joe’s adventure squad

A great way to explore Greenwich, we all really enjoyed it! Fun and challenging clues to keep us guessing, highly recom…

PRAA Chicago escape room


great way to explore the city we have just moved to!

Team Hammond Chicago escape room

Team Hammond

We had a great experience! Cambridge is our local City, but we were amazed at how much we'd never seen within such a sm…

The RamSchals Chicago escape room

The RamSchals

Great day out with kids (age 10-12). We loved it!

Woolpack Meadows explores Chicago escape room

Woolpack Meadows explores

What a fantastic opportunity to have fun and explore York. Thoroughly enjoyed it. Thank you

Toiyub + Amber Chicago escape room

Toiyub + Amber

Amazing experience, it’s something different to do and you get to explore the history of Manchester. I would highly rec…

GOLD Chicago escape room


Excellent way to discover parts of London we did t know existed even as a Londoner and fun with friends

Stweam Chicago escape room


We had an absolutely fabulous afternoon working out the clues and searching high and low for the answers!! We'll defini…

Read all our customer reviews

Ready? Book your Chicago escape room today

The “Fresh” Way To Experience A Chicago Escape Room


Change is here, Chicago - and it starts with you.

Your Chicago escape rooms should push as many boundaries as you. 

At CityDays, we create escape rooms in Chicago that go further - and we mean that literally. We’re all about finding new ways to take on challenges, solve puzzles and unravel fiddly riddles…

But our Chicago escape rooms reveal more than just your competitive streak. 

You still get all the puzzles, riddles, cryptic clues and challenges of a traditional escape room, with an added twist. 

We bring the games outdoors, where you and your friends, family, coworkers and more get the chance to expose historic neighborhood secrets, solve mysteries, and much, much more… 

No doors. No ceilings. No specific time slots. No hassle. That’s the CityDays way!

Urban Escape Rooms Chicago: An Outdoor Extravaganza


Chicago, you’ve been sleeping on a mystery that’s right on your doorstep. 

This is your chance to unravel your city once and for all - one challenge, riddle, and puzzle at a time.

At CityDays, we create treasure and scavenger hunts, walking tours and outdoor escape rooms that push the limits. 

Through a mixture of painstaking research, some humble creativity and a healthy dose of ambition, we provide people like you with games they’ll never forget.


We love the philosophy of traditional escape rooms - you know, working together as a team, solving puzzles, deciphering riddles, all that stuff! But we fundamentally disagree with one point: that you have to be inside to do it.

So we did something crazy: we created our own games and took them outdoors. And that’s not all we did, either.

Our Chicago escape room games are a little different from what you might have played before. Let us fill you in…

CityDays’ Outdoor Chicago Escape Rooms: A Live-Action Game in Downtown Chicago


Before you play one of our Chicago escape room games, there are a few things you should know.

CityDays’ outdoor escape room games are “built” differently. Since you’ll be outside, you won’t be breaking out of a room. You’ll be doing so much more than that.

You’ll be opening the lid on Chicago’s city secrets, its history and its culture.

You’ll be working as a team to solve puzzles, riddles and challenges that bring you closer together.

You’ll solve puzzles that result in meaningful information. 

You’ll interact with Chicago and immerse yourself in your surroundings.


The whole premise of our trails is to encourage more people to get outside, explore more, reevaluate their surroundings and - most importantly - have a lot of fun. 

We transform cities into playgrounds by creating routes and puzzles from zero that are designed to test you and your puzzle-solving, teamwork and observation skills, based on the city in question - in your case, Chicago. 

Your mission is to crack the puzzles, challenges and cryptic clues we’ve provided for you. 

You’ll have to use your powers of deduction, wit and guile to complete the game. Brains, not brawn, will win you and your team the top spot on our Chicago leaderboard.

Stick with us to find out how it works… 

How Our Outdoor Escape Rooms Chicago Work


Our Chicago escape “rooms” are created from scratch and involve a slightly different strategy than typical escape rooms. 

Luckily, it’s very simple to explain them.

First things first, the games are held outside

Once you’ve picked your route, we’ll send you the start location to you via WhatsApp, and you’re free to start playing whenever you want

From there, you’ll be sent a set of tasks, puzzles and riddles, each containing clues for you to decipher. 

Clues come in all different shapes and sizes, and every member of the team is needed to come up with the correct answers. They could reference anything from street art to street furniture, plaques, statues or even building quirks themselves.

If you don’t give us the right answer, you won’t move on in the game! 

When you’ve sent us the correct answer, you’ll be given new clues and challenges to lead you to your next destination. Each location is located a short walking distance away, and may require you to keep your eyes peeled for possible clues along the way…

Once you’ve answered all our clues, visited all the destinations and completed the trail, we’ll tally up your score. This is based on how many correct answers you got, any time penalties you accrued, and how many hints you asked for. 

All you need to play our games is a phone with WhatsApp, access to cellular data and a pair of comfy shoes. That’s it!

Any questions? Here’s how it works.

Outdoor Escape Room Downtown Chicago: An Adventure On Your Doorstep


The awesome thing about our Chicago escape room games is they’re easily accessible and you can start playing whenever you want. 

You don’t need any previous experience of escape rooms, prior knowledge of Chicago or any fancy equipment. You don’t even have to book a specific time slot to play our games (perfect if you have short notice to entertain a bunch of people!). 

And just so you know, our games are perfect for bachelor and bachelorette parties, work events and team building activities, birthday parties, or just as a fun thing to do with your partner, friends or family. 

Team-Building Outdoor Escape Room Games in Chicago

We’re proud to say that we’ve helped many businesses around the world plan better, more exciting and more sustainable team-building activities for over five years. 

Will your business be next?

Our team-building activities in Chicago have been designed to boost your team bonds, heat up your colleagues’ competitive sides and teach them a thing or two about the city they live and work in.

We offer premade routes and bespoke trails that cater especially to your businesses’ needs. 

So if you want to start or finish at a particular venue, that’s no problem. 

If you need to stop by somewhere specific - we’ll add it in. 

And whether you have a team of five or 500 to organize, we’ll do it all for you. 

Challenges are at the heart of our Chicago escape room games, so it’s only fair that you challenge us in return. 

Send us your queries and put us to the test! 

The Best Outdoor Escape Rooms in Chicago

Here are our available games and outdoor escape rooms in downtown Chicago!


Lost in The Loop

Dive into "Lost in The Loop," an outdoor escape game set in the heart of Chicago's North Loop, where the city's iconic architecture and art take center stage. 

This engaging experience, blending the thrill of an escape room with the discovery of a walking tour, leads you through a series of puzzles, challenges, and captivating stories about Chicago's transformation from a modest farm to the bustling metropolis it is today.

Uncover the history behind some of the city's most remarkable landmarks, including the Tribune Tower, Plaza of the Americas, Herald Square, its oldest skyscraper, and a location rumored to have been a speakeasy run by Al Capone. This journey is packed with intriguing puzzles, exciting challenges, and stops at the finest bar and cafes, offering plenty of surprises along the way.

"Lost in The Loop" is an immersive adventure perfect for exploring the hidden nooks and crannies of the North Loop, revealing the unusual and secretive sides of Chicago. Whether you're a local or a first-time visitor, this game promises a unique way to experience the city's rich history and architectural beauty.

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