⭐⭐⭐⭐⭐ 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.
Tom was great! He was very informative but fun. He was very well prepared and seeing the city through his eyes helped us enjoy the rest of our trip so much more!
MeghanTom was a fantastic guide on the out-of-the-way city tour. We learned so much! He’s incredibly knowledgeable and so generous in answering questions. We could not have asked for a better tour and are glad it was tip-based. Thank you,… read more
ChristyTom was very professional and knowledgeable! My husband and I went on the Christmas tree lights tour. We did not know about the many trees inside various hotels throughout the city, and we are grateful we did the walking tour.… read more
VinaPerfect 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.
