⭐⭐⭐⭐⭐ 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!
MeghanWe 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
PhillipWe had a fantastic tour with Tom! We took the total loop tour and learned so much about Chicago – past, present, and future. He took us to many key landmarks in the city and showed us some beautiful photography… read more
KimberlyPerfect 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.
