Explore Chicago's
Greatest Stories
Expert led tours thought the neighborhoods, history and character that make this city legendary. Reserve your spot today.
⭐⭐⭐⭐⭐ 5.0 on Google · 800+ Reviews
🏆 2025 TripAdvisor Traveler’s Choice Winner
As Seen In: MSN · Budget Travel
SIMPLE AS IT GETS
How Our Tours Work
Register online. No Cost. No Stress. Just show up, explore and pay what you the experience was worth
1
Pick a Tour & Register
Browse tours below or view our full tour calendar. Each tour covers a different route and theme. From gangsters to architecture to neighborhoods.
2
Show Up
Arrive at the meeting point a few minutes early. Our guides are easy to spot – look for the group gathering at the landmark and our famous red shirts.
3
Enjoy the Story
Each tour provides 2 hours of captivating storytelling, insider knowledge and Chicago characters you won’t hear about anywhere else.
4
Pay What It's Worth
At the end, tip your guide directly. Most guests tip $15-$25. This is how they make their living.
Find Your Chicago Story
Choose from our most popular tours — each one free, led by a passionate local guide, and approximately 2 hours.
Chicago Crime & Gangster Tour
Journey through Chicago’s notorious past — Prohibition-era mob haunts and legendary gangster hideouts in River North and the Loop.
Chicago Riverwalk & History Tour
Stroll along the Chicago River discovering iconic landmarks, from DuSable Bridge to the stunning Tiffany Glass dome at the Chicago Cultural Center.
Chicago Total Loop Tour
Stroll through the heart of Chicago — from the Sears Tower to Millennium Park, uncovering the architecture and stories that define the city.
Unique Chicago — Off the Grid Tour
Skip the tourist trail and discover Chicago’s most Instagrammable hidden gems, from Death Alley to the breathtaking Tiffany Glass Dome.
Magnificent Mile Tour
Step into Chicago’s golden corridor along North Michigan Avenue, where historic landmarks, luxury shopping, and architectural wonders converge from Lake Michigan to the Chicago River
Pedway Underground Tour
Stay inside and warm on the Chicago Pedway Tour, discover the fascinating “city below the city” used by Chicagoans every day—the Pedway.
Loop Interior's Tour
Everyone sees Chicago’s skyline. Almost nobody gets inside it. The Loop Interiors Tour takes you through the interiors of some of the most architecturally significant buildings in the world.
Architecture Tour
Our Loop & Architecture Tour winds through Chicago’s Loop district giving our guests and up close and personal experience of some of the world’s most influential and gorgeous buildings.
Gold Cost Tour
Chicago’s Gold Coast is one of the city’s most iconic neighborhoods. With the shores of Lake Michigan on the east, this is one of the most expensive zip codes in all of Illinois.
Holiday Lights & Tree Tour
Chicago during the winter holidays is truly magical! Make some holiday memories as we walk along city streets, lined with trees, lights and gorgeous window decor.
Loop & Public Art Tour
Chicago is home to more than 500+ pieces of public art in more than 150 municipal facilities across the city.
What Our Guests Are Saying
Tom was an excellent guide for the Chicago Loop Tour and extremely knowledgeable and you could tell he enjoyed telling us about the history of the different sights, buildings, and sculptures. Highly recommend if you have a few hours to… read more
JenOur tour with Tom on a brisk Thursday was informative and well worthwhile, even for a “local” like myself. Tom’s love of Chicago was on full display and the energy in our small group was high even with high winds!
BrianWe had an amazing great architecture walking tour with Tom! Tom was an amazing guide and super informative and knowledgeable about the Chicago skyline. This tour is a really great way to see the city and get your bearings. I… read more
PhillipExperience Chicago Privately
Perfect for schools, corporate groups and get togethers. Our private guides deliver an intimate, personalized Chicago experience tailored entirely to your group.
Starting at just $250 for up to 20 people — the most competitive private tour rates in the city.
Ready to Explore Chicago?
Check our current schedule and book your spot in minutes. All tours are free — just pay what you think the experience was worth at the end.
GOOD TO KNOW
Common Questions
Do I need to book in advance?
We recommend booking in advance through our online reservation system to secure your spot, especially during peak tourist season (spring through fall). Walk-ups may be accommodated based on availability, but booking ahead guarantees your place on the tour.
Are the Chicago walking tours really free?
Yes — our tours are completely free to join. We operate on a tip-based, pay-what-you-wish model. You decide what the tour was worth to you at the end. If you loved it, tip your guide accordingly. If you didn’t enjoy it, you owe nothing. We don’t want you to pay unless you feel the tour was genuinely valuable.
How long are the tours?
Most of our guided tours last approximately 2 hours. The self-guided Crime & Gangster Tour covers about 1.8 miles and typically takes 90 to 120 minutes to complete at your own pace.
Are the tours family-friendly?
Yes, our guided neighborhood and architecture tours are family-friendly and suitable for all ages. The self-guided Crime & Gangster Tour discusses Chicago’s organized crime history and may be more appropriate for teens and adults.
What if the weather is bad?
Tours run rain or shine. Chicago weather is famously changeable, so bring layers. A little drizzle has never stopped a great story.
Do you offer private walking tours of Chicago?
Yes. We offer fully customizable private Chicago walking tours for groups of up to 25 people. Private tours start at $250 and can be tailored to your group’s specific interests, schedule, and neighborhoods. They’re a great option for corporate groups, family reunions, school trips, bachelorette parties, and other special occasions. Request a private tour here.