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Chicago Walking Tours

  • 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
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 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

RuddRobins Chicago walking tour


Wonderful way to explore, Nottingham next!

Mayo for Sam Chicago walking tour

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? Chicago walking tour

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 Chicago walking tour


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 Chicago walking tour

Definitely Maybe

Excellent experience. Really quick messaging and challenging but fun clues

Dally101 Chicago walking tour


Myself and my partner really enjoyed this activity. I'm from Scotland and he is from outer London and both found it a g…

Team London birthdays Chicago walking tour

Team London birthdays

We had a really great time! Really made my birthday!

TJT Chicago walking tour


Such a unique and fun experience! It really allows you to see parts of the city that you wouldn’t necessarily visit! In…

Ru and Coel Chicago walking tour

Ru and Coel

It was amazing getting to tour all the little details of Sydney while having an underlying story and puzzles to solve! …

Princess Squeak & the Silly Goose Chicago walking tour

Princess Squeak & the Silly Goose

Such good fun, clever clues, and the trail took us to see parts of York we have never seen before! Loved it!

The Band on Tour Chicago walking tour

The Band on Tour

A really fun day out. Got to see lots of the city and learn some interesting facts too!

Blakemores on Tour Chicago walking tour

Blakemores on Tour

Excellent way to see the city

Joe’s adventure squad Chicago walking tour

Joe’s adventure squad

A great way to explore Greenwich, we all really enjoyed it! Fun and challenging clues to keep us guessing, highly recom…

PRAA Chicago walking tour


great way to explore the city we have just moved to!

Team Hammond Chicago walking tour

Team Hammond

We had a great experience! Cambridge is our local City, but we were amazed at how much we'd never seen within such a sm…

The RamSchals Chicago walking tour

The RamSchals

Great day out with kids (age 10-12). We loved it!

Woolpack Meadows explores Chicago walking tour

Woolpack Meadows explores

What a fantastic opportunity to have fun and explore York. Thoroughly enjoyed it. Thank you

Toiyub + Amber Chicago walking tour

Toiyub + Amber

Amazing experience, it’s something different to do and you get to explore the history of Manchester. I would highly rec…

GOLD Chicago walking tour


Excellent way to discover parts of London we did t know existed even as a Londoner and fun with friends

Stweam Chicago walking tour


We had an absolutely fabulous afternoon working out the clues and searching high and low for the answers!! We'll defini…

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.

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