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.
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.
Our tours cover Chicago’s most iconic neighborhoods and landmarks including Millennium Park, The Loop, the Chicago Riverwalk, and Lincoln Park. We offer tours focused on architecture history, gangster history, and neighborhood exploration. Tours run 7 days a week. Visit our Tours page to see the full schedule and book a spot.
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.
Meeting points vary by tour. Each individual tour page on our website lists the exact meeting location and nearby landmarks or transit directions. We recommend checking your specific tour’s page before heading out.
Our tours run rain or shine in most conditions. We recommend bringing a rain jacket or umbrella. In the case of severe weather, we will communicate cancellation or rescheduling information to all registered guests.
Our tours are led by a team of experienced, locally based guides who share a genuine passion for Chicago. Several of our guides hold the Certified Tour Guide (CTG) credential through the Chicago Tour Guide Professional Association — a rigorous three-part examination process that takes approximately one year to complete. Collectively our guides have led hundreds of tours for guests from over 100 countries and all 50 states.
Yes. Several of our guides hold the Certified Tour Guide (CTG) credential from the Chicago Tour Guide Professional Association. This certification requires passing a comprehensive three-part examination covering Chicago history, architecture, geography, and tourism.
We are Chicago’s only locally owned and operated free walking tour company. Unlike large tour operators, we are an independent small business with deep roots in the city. Our guides are passionate locals — not employees reading from a script — and our pay-what-you-wish model means we are motivated to give you the best possible experience every single time. We have earned 1,300+ five-star reviews from guests across more than 50 countries.
Tipping is entirely up to you and based on your experience. A common range for a tour you enjoyed is $10 to $20 per person, but there is no set amount and no pressure. The beauty of the pay-what-you-wish model is that you decide the value.
No — there is no booking fee or deposit. Reserving your spot is completely free. You only tip at the end of the tour, and only if you felt the experience was worth it.
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.
Visit our Private Tours page and fill out the inquiry form with your group size, preferred date, and interests. We’ll work with you to design a custom Chicago experience.
We recommend wearing comfortable walking shoes. Chicago weather can change quickly, so dress in layers and check the forecast before your tour. Bring water, especially in summer. Our tours cover several miles of city streets, so comfort is key.
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.
Chicago’s Loop and Riverwalk areas are generally accessible, with sidewalks and paved surfaces throughout. If you have specific accessibility concerns, please contact us before booking so we can advise on the best tour for your needs.
Yes. We are a member of the Free Tour Community, a global network of independent, locally owned tour operators running on the pay-what-you-wish model in cities across the United States and around the world, including New York, San Francisco, and Seattle.
The best way to reach us is through the contact form on our website or by visiting our Tours page to book directly. We look forward to showing you Chicago!
