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
Chicago Chinatown Hunt
A hunt to hit all the senses… more
change the date, time, number of people or game.
- 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.
Chicago Reviews
The great things you say about CityDays Chicago walking tours
BirchScar
Such a cool experience, letting us really learn the city. Gave us a ton of steps, and introduced us to the best place t…
The gals
Very good day, went to places we never knew existed, and amazing food!
UC
fascinating and scenic walk away from the main drag with great pubs for breaks. Great to explore a lesser known part o…
Big Bois
This was such an enjoyable experience, it felt like we were doing the amazing race!
Vagrants
Had a great time all round Whitechapel, trying to work out who Jack the Ripper was. These days out are a great way to s…
Cousin Crew
Thoroughly enjoyed our family day out. We learnt so much about our beautiful city.
HonkerVille
Had a great time solving some at times tricky clues and finding some hidden gems
Souper Nerdz 🤓
So much fun! Really interesting trail, educational and fun! Would definitely do one of these again! :)
Kiscons
Whole thing was amazing - we thoroughly enjoyed it - some clues were tough but we managed to crack them - definitely lo…
Team Starlight.
We had a great time following the clues and exploring London! Thanks very much, we’d thoroughly recommend it 👍
estrogen hunters
honestly we had a blast and this has quickly become my favourite outing in sydney im so fr, my friend and i are obsesse…
The Kayakers
Great trail, lots of fun, and learned something too!
THE GAYS
It was great! Helped us appreciate our city with all the nooks and crannies and alleyways. We really enjoyed the walk f…
Half 10
Fantastic day learning more about our home city and the rain actually made it more enjoyable with plenty of laughs
Detectives PeekAtChu
Fun day out exploring g the city!
ZweiMausensundOtto
Nice, it was so much fun. We would absolutely do it again.
AussieDane
We loved the day, but we flagged a bit as it got hotter and the day wore on (we did do a bit of shopping in there, so …
Birthday Puzzlers
Well considered clues that weren't too difficult but still challenging - with smatterings of humour.Introduced to new i…
Misfits
OMG! What a brilliant day. We saw parts of London we hadn't seen and learnt information about Jack the Ripper we didn't…
Team PR
We live close to London so are regular visitors. With our children we wanted something different as we had done most th…
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.
