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Chicago Walking Tours

  • Work together to solve fun challenges & puzzling clues
  • Guided by clues sent to your phones
  • Explore Chicago's historic landmarks and hidden gems
  • Discover top-rated pubs, bars and cafes
  • Compete 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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Rated 5/5 on Google
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Rated 5/5 on TripAdvisor

Action-packed Chicago walking tours 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 walking tour.

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 walking tour. Even stop and start once you've begun.

Fun activity for all groups

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Chicago walking tour Reviews

The great things our customers have to say about CityDays Chicago walking tours

Carolines over 50's Club Chicago walking tour

Carolines over 50's Club

Fantastic trail , really enjoyed 10/10

Golden Pineapple Chicago walking tour

Golden Pineapple

Amazing experience. Great ways to show little nooks and crannies you would otherwise miss. Really fun clues. Would full…

MAD MAX Chicago walking tour

MAD MAX

Beautiful experience, group absolutely loved it. Great history and storyline, only thing is that there could’ve been mo…

Candler Clan Chicago walking tour

Candler Clan

Had a fantastic day out! We loved the clues and they were the right level of difficulty for the whole family - age 11+.

The Ginger & the Gay Chicago walking tour

The Ginger & the Gay

David and I had the BEST day exploring York, solving the clues, and had such a wonderful time over the whole day. What…

Mumson Chicago walking tour

Mumson

Had a great day out in London doing the outdoor escape room, I have been round London hundreds of times but found areas…

Shell and Phil Chicago walking tour

Shell and Phil

Brilliant clues and a great way to see the city. We will be looking to see which other cities we can do this in!

The Gunners Chicago walking tour

The Gunners

We had a great few hours following the clues and exploring a part of London. Definitely tested the brain cells! Loved i…

Brains and Whiston Chicago walking tour

Brains and Whiston

Was a intresting and fun filled day 😁. FromBrains & whiston

Special six Chicago walking tour

Special six

A fantastic day out finding new places and spotting things you would normally just walk by! Highly recommend this activ…

Rocky Chicago walking tour

Rocky

Great for getting out and seeing parts of the city you wouldn't other wise see. Plenty of places for food and drink on …

Wiggins and Simpsons Chicago walking tour

Wiggins and Simpsons

Such a great time. We had an amazing afternoon, and enjoyed all the stops along the way!!

Priceless Chicago walking tour

Priceless

Great way to explore London. Even if you live here you will discover hidden gems and lots of fun facts

Rescue Aid Society Chicago walking tour

Rescue Aid Society

Fantastic day out! Wet and windy, but helped us see a city we are familiar with in a whole different light! Great fun!

Kanye Quest Chicago walking tour

Kanye Quest

Very fun to see some areas where we've never been! Good riddles, not too hard but not too easy.

Team PP Chicago walking tour

Team PP

It was fantastic! Really interesting clues and made me see my home town in a new way - looking for our next one!

BBSS Chicago walking tour

BBSS

It was really excellent experience. We saw lots of places we had never seen and enjoyed the challenge of the clues. We …

A and L Chicago walking tour

A and L

We loved the tour! Made us think, tired us out and was great fun! Thank you

Callaghans Chicago walking tour

Callaghans

What an excellent way to explore Bath. We had great fun following the clues and finding all about the city. Brilliant w…

SBM Chicago walking tour

SBM

Was a fantastic day out! Cannot fault it. Got us thinking, was the right level of challenge, and took us to some beauti…

Read all our customer reviews

Ready? Book your Chicago walking tour today

See More, Do More, Learn More with CityDays

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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

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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.

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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

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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

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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…

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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.

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