Chicago Walking Tours
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 Chicago walking tours
Team Private LRJH
Great team day out. Lots of fun!
Diana & Nath
Absolutely loved it, it was better than I imagined. So much fun and a great way to see the city. The icing on the cake …
The Toomey Two
Fantastic experience, thoroughly enjoyed it and allowed us to see Manchester through new eyes whilst having fun at the …
The Perimenopause Pioneers
We had such a fun day , racing across Manchester , girls vs boys . We were engaged from the moment it started till the …
JVenture
Absolutely fabulous experience! We really enjoyed the whole day. Would highly recommend!
Team Nova
Such A great adventure. Saw places I never knew existed and loved the challenges. Brought us all together!
Ride or Die
Had the best day , got a lot of steps in but was so fun!!
HD9 Explorers
A great day enjoyed by the whole team. It exceeded our expectations thanks. A fab way to see previously unseen parts of…
Chummy’s
Was the best day out! Found so many little streets and was a fab way to explore different parts of the city!
The White Roses
Had such a good time playing yesterday! Would recommend and already looking forward to trying it out in London!
THE ONE ARMED BANDITS
This was the wettest day in Manchester for the whole of 2025. What did we decide to do? We booked Race Across Mancheste…
Touched by an Uncle
Really good day, we had to call it off early just because of the stormy rain and was getting too late, wish we could ha…
Awesome Foursome + 1
Excellent adventure on Julie's birthday... we had a blast! Would definitely do this again. Awesome Foursome + 1
Dragons
My daughter bought this for my birthday treat. I didn’t know what to expect. Fortunately it was fantastic fun and a gl…
Raytains
An excellent day out around London. We saw parts of london that we hadnt been to before. A brilliant mix of problem so…
Bumbu
The treasure hunt was super fun! Didn’t feel too short or too long and the clues were challenging enough but not imposs…
The Millwardians
Great day out, although the rain was biblical, which slowed us down dramatically, using the phones and walking around,…
Alan’s Crew
Great job and clues. Loved exploring London in a different way.
How old’s Paul?
Team ‘How old’s Paul’. We had a fantastic day. An incredible event which we all found really enjoyable. Birthday gift f…
Agents J & K
A whole lot of fun exploring London. Got more competitive as we bumped into other teams and the running started. Great …
Ready to see lots of smiling faces? Read all our customer reviews
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
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.
