⭐⭐⭐⭐⭐ 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.
We had alltogether three tours in chicago, all hosted by Tom. He did a great job, he was very entertaining and even changend some parts of the routes to minimize overlap. Highly recommended!
DietmarToday I went on the tour of Chicago with Tom as my guide. We were a group of 19 and it was a beautiful Spring day in the city. Informative, funny, historical, interesting, and clever. After 2+ casual walking hours… read more
TomTom was a great tour guide! Informative and passionate it was an easy 2 hours of walking and learning! This atrium was my absolute favorite on the tour and I was blown away to see Floyd Wrights remodeling work! Thank you… read more
AbigailPerfect 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.
