⭐⭐⭐⭐⭐ 5.0 on Google · 800+ Reviews
🏆 2025 TripAdvisor Traveler’s Choice Winner
As Seen In: MSN · Budget Travel
Choose from our most popular tours — each one free, led by a passionate local guide, and approximately 2 hours.
Journey through Chicago’s notorious past — Prohibition-era mob haunts and legendary gangster hideouts in River North and the Loop.
Stroll along the Chicago River discovering iconic landmarks, from DuSable Bridge to the stunning Tiffany Glass dome at the Chicago Cultural Center.
Stroll through the heart of Chicago — from the Sears Tower to Millennium Park, uncovering the architecture and stories that define the city.
Skip the tourist trail and discover Chicago’s most Instagrammable hidden gems, from Death Alley to the breathtaking Tiffany Glass Dome.
Jeffrey, our guide,for the Free Chicago Walking Tours, was fantastic. He was enthusiastic, knowledgeable, and safety conscious. We focused on Millennium Park but learned a lot about Chicago history and early peoples as well. About 90 minutes and approximately a… read more
JohnsonWe 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
Phillip⭐️⭐️⭐️⭐️⭐️ Even in the rain, Tom made Chicago shine 🌧️✨ Yesterday, my friend Carolin (visiting from Stuttgart, Germany) and I braved the rain for a Free Chicago Walking Tour — and it was 100% worth it. Tom was not only incredibly knowledgeable,… read more
LarryPerfect 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.
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.
