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
- Coming soon, get notified
Magnificent Mile
change the date, time, number of people or game.
- Coming soon, get notified
Chicago Old Town
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.
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
SameLeon
We did the Greenwich adventure and we really enjoyed. We saw places that we would have not probably never seen and lear…
Rumors Got A Boyfwend
An amazing day out! Great clues and so fun to explore the city in a unique way!
The K Team
Amazing day! We really, really enjoyed the whole day!! The game was so clever! The only thing was, one of the clues (a …
Burlesque
We had a brilliant time. Saw lots of London that we have not seen before. Already booking the next one.
Team NT
We had a blast exploring the city. Such a fun way to see discover London and learn some of the history. The cryptic clu…
Penny Dreadfuls
Mum and I LOVED our time out in York, exploring bits we don't think we'd have noticed without CityDays guiding us there…
Jenny
We did like the quest very much! The interface was easy to use and was helpful.My wife really loved the dog fountain an…
DJ's
Fab way to get to know the city better. Clues were easy to follow whilst making you take in things you've never noticed…
Big Three O
We had a great afternoon. The clues were enough of a challenge to make it fun- but not too hard! We loved the walk and …
Tabitha Peat
Great experience. Had way more fun than I was expecting and got quite competitive!
JerseySpuds
Really good clues and learnt new things so it parts of London. Great fun!!
cheeky buggas
It’s soooo fun
Sanlo
We had a great day in Brighton! We have been there before but did not know such incredible streets and little squares e…
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.
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.
