⭐⭐⭐⭐⭐ 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.
⭐️⭐️⭐️⭐️⭐️ 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
LarryOur 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!
BrianTom 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
JenPerfect 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.
