Chicago Walking Tours
Urban adventures bringing the secrets of Chicago 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 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
Next Steps
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- 1. Select your game, pick a trail of your choice and receive your welcome email.
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- 2. Rally your team and enter a team name and phone number(s) into the system.
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- 3. Receive your welcome text, then head to the start location on a day and time of your choice.
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- 4. Text START to receive the first in a series of cryptic directions. Solve the puzzles to unravel your mystery.
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- 5. Discover unique places, the secret and hidden of your city - and great independant pubs/cafes!
Don't have a great time?
Simply let us know why and we'll refund you in full.
CityDays Chicago Hunts
Each hunt explores a different area of city in one of two ways. Our classic treasure hunts & scavenger hunts use puzzle-filled directions to guide players to exciting new sights. Our Story trails do all this with the added bonus of an immersive story on top - play the main character and relive a tale from the city's past or experience a story all your own.
Lost in the Loop
change the date, time, number of people or game.
- Coming soon, get notified
Chicago Chinatown Hunt
change the date, time, number of people or game.
- Coming soon, get notified
Magnificent Mile
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- Coming soon, get notified
Chicago Old Town
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Action-packed Chicago walking tours 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 Chicago walking tour.
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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 Chicago walking tour. Even stop and start once you've begun.
Fun activity for all groups
Chicago walking tour Reviews
The great things our customers have to say about CityDays Chicago walking tours
Margaretta Pirates
Honestly, I did not know what to expect from this experience. I booked it as a mystery day to surprise my mom and siste…
Team McReady
A great day out with clues that were not too easy and not too difficult. Would recommend!
Muppets
Just the right amount of information when clues are solved. Stops are important. How about some images with the trivi…
Odyssey
We had a brilliant day together, great fun as a group, and even the seasoned Londoners saw sights they'd never seen bef…
The Shaws
Great day out for a family of 4 (22 and 17yr old) we all thoroughly enjoyed it, Greenwich is stunning thank you
Bros from other hoes
We booked Clause & Effect for our family when they were visiting from the South West and had the best time (and scran!)…
S'us
Wonderful fun! Trail was well thought out and just difficult enough to give our brains a work out as well as our legs.
Willow
Amazing day out. We’ve done both the Leeds walks now and both were brilliant. Planning on York next!
Cirque du Sore Legs
Loved this!!!!! Super fun! We will be doing this again
Ailbhe & Anne
So much fun, challenging in the best way and opens your eyes to such an interesting side of the city!
Veronica Hein
So fun! Loved it.
Bowen Weather-Banton
Loved the walk, especially the view from the Observatory:) will definitely be coming back to Greenwich now
Monocle Editors
A really interesting and enjoyable mixture of London history, puzzles at just the right level of challenge for a Sunday…
Griffin Girls
This was an excellent way of exploring the city. We thoroughly enjoyed it.
The Red Folk
Great fun. Learned some things I didn't know about Birmingham.
RuddRobins
Wonderful way to explore, Nottingham next!
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?
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
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
Excellent experience. Really quick messaging and challenging but fun clues
Ready to see lots of smiling faces? Read all our customer reviews
Ready? Book your Chicago walking tour today
See More, Do More, Learn More with CityDays
Welcome to the Windy City, a city of industry, ingenuity and incredible history!
As the United States’ third most populous city, Chicago is a city that buzzes with stories, landmarks and pioneering figures.
Whether you’re a curious Chicagoan on a mission to discover your city’s roots or a visitor to Chi-town hoping to explore, we want to show you the best history, culture and interesting facts that Chicago has to offer - all on your own terms.
Self-Guided Walking Tours Chicago: See Chicago Your Own Way
At CityDays, we design our Chicago walking tours differently. We’re dedicated to elevating your sightseeing experience, so we’ve combined all the stuff you’d expect to see with a bunch of cool, hidden stuff along the way.
Oh, and did we mention you have to navigate your own way there? It’s not as scary as it might sound.
Our self-guided Chicago walking tours get you interacting with and learning about Chicago’s streets, landmarks, history and famous figures just like any other walking tour. To set ourselves apart, we’ve tweaked the typical approach to turn your walking tour into an adventure.
Here’s how:
You’re in charge. Our Chicago self-guided walking tours put you at the center of your adventure. This means it’s up to you when you do your tour, who you do it with, if and when you want to take breaks and where you stop to recharge your batteries or take a look around.
Solve our puzzles, uncover Chicago. Think of you and your team of friends, family, or colleagues as detectives, tour guides and explorers. With us, you navigate your way around Chicago by answering puzzles, riddles and finding clues based on your surroundings.
No strangers, no impossible-to-hear tour guide. We send clues directly to your phone in a text message format, so there’s no need to strain your ears to hear above the noise of traffic, day-to-day conversations or other people on your tour chatting through a guide’s explanations. It’s just you, your chosen teammates and Chicago’s secrets!
Freedom’s the word. From the moment you start your Chicago walking tour until you finish, you’re guaranteed to learn, have fun, make memories and get some fresh air and exercise.
Got any questions? Here’s how it works.
Self-Guided Chicago History Tours: Agriculture, Architecture and Al Capone
Learn about Chicago’s varied and often striking history with a CityDays walking tour!
Named by the Native Potawatomi people due to the area’s abundance of wild garlic, Chicago has been completely transformed over the past couple of centuries.
From fur trading to farming, 1920s gang crimes to becoming a home to former US President Obama, Chicago has seen its fair share of history - and we want to share it with you!
Our Chicago walking tours take you on an exciting journey through Chicago’s historical timeline in a way that celebrates the city’s cultural quirks and mysterious facts. Along the way, you’ll discover street art, cool bars and much, much more.
By playing along on our CityDays Chicago walking tours, you’ll be exposed to all things architecture, plenty of art and even the site of an alleged speakeasy run by Al Capone himself…
The Best Chicago Walking Tours
No lines, no waiting around, no hassle.
That’s part of what makes CityDays’ Chicago walking tours the best in the city.
All you need for your tour is a good pair of walking shoes, a fully charged phone with data access and a sense of adventure.
We recognize that this is your day out - not ours. So it’s up to you how it plays out: compete for first place on our leaderboard or take your time and really soak up the sights. Either way, we’re only a text message away if you get stuck.
Available Trails and Chicago Walking Tours
Interested in finding out more about the kinds of self-guided historical Chicago walking tours we provide? Here’s where you get a tiny sneak peek into what to expect on your next adventure with us…
Lost in The Loop
Uncover the architectural splendor and artistic allure of Chicago's North Loop with a puzzle-filled adventure that melds the excitement of an escape room with the discovery of a walking tour.
Explore how Chicago evolved from a simple farm to a bustling city housing one of Picasso's most unusual sculptures. Key sights include the Tribune Tower, Plaza of the Americas, Herald Square, the city's oldest skyscraper, and a location rumored to have housed a speakeasy owned by Al Capone…
With a mix of puzzles, challenges, stops at excellent pubs and cafes, and unexpected discoveries, this interactive exploration of the North Loop is a fantastic way for both locals and newcomers to uncover the strange and hidden secrets of Chicago, right in plain sight.
Ideal for groups of friends, families, or colleagues, this Chicago walking tour takes you through the area's historic highlights and lesser-known spots, enlivened with challenges, puzzles, and intriguing facts.
