CHICAGO · ILLINOIS
The best of Chicago.
The 15 most popular guided tours in Chicago, from river-architecture cruises and skyline decks to gangster trails and food walks.
A 90-minute Chicago River cruise with architecture narration, indoor climate control, and major-sight views of Wrigley Building, Marina City, and more.
Most Popular“We had a great time. The guide we had was great and explained the history and other great information along the tour. A great way to see the city and get some history too”
A historian-led Chicago Loop walk mixing Prohibition-era mob stories and reported ghost sites, with optional minibus upgrade for $52.
“Taka our guide was very knowledgeable about the history of area. The tour was managed time wise and we were all able to know what we were doing and stay together. I learned a lot about the area that I had never knew about before. She spoke so everyone could hear her in the busy…”
A $49 coach tour through Chicago’s mob history with photo stops, mini museum, and story-first guides. 90–120 minutes of crime scenes.
“Lots of great info and stops bring it all to life. Recommend highly. Our guide was full of extra tidbits and interactive.”
Take a 45-minute Chicago River architecture cruise from the Magnificent Mile with live narration, top-deck views, and major landmarks.
“Lots of information. You can stay inside downstairs or be up on the deck to look up at the buildings. Just the right length of tour. Very convenient.”
One-and-a-half-hour Chicago architecture boat tour with live narration, River and Lake Michigan views, skyline photos, and climate-controlled seating.
“Very informative. Bring a small blanket- it was chilly. But if you’re hot, you could sit on the blanket. The chairs were pretty uncomfortable.”
Hop-on, hop-off Big Bus Chicago gives you open-top views, audio commentary, and easy stops at top sights with 24/48/72-hour flexibility.
“Candace was exceptional. She was very knowledgeable and spoke clearly. Her playful personality made the tour very enjoyable.”
Taste Chicago classics on a 3-hour walking tour with deep-dish, Italian beef, hot dogs, brownie and popcorn plus a free 2-hour bike or kayak.
“Go hungry, plenty to eat. Our Tour guide was funny, entertaining, and very knowledgeable about Chicago.”
Join a historian-led Chicago South Loop tour blending gangster lore and ghost stories, with stops at Riverwalk, theatres, and haunted hotels.
“Sophia was a delight! This was my favorite tour of this trip. So much knowledge and lore crammed into 2 hours. A must for true crime, history, and ghost story fans.”
A 90-minute Chicago River architecture cruise with live narration, covered seating, and big skyline moments from Wrigley Building to Navy Pier.
“I scheduled a trip for Saturday Oct 18th, paid my fees, and less than 24 hours out the tour company canceled the trip and would not refund me. The listing said the tour was rain or shine, so I was prepared to go regardless. It was a beautiful day, they canceled the trip, and would…”
A 2-hour Loop walking tour focused on jaw-dropping building interiors, ending at Chicago Cultural Center, with a local guide for $35.
“It was a wonderful experience. I gave the experience to my girlfriend as a birthday gift and activity. She loves walking tours. Andrew was funny informative and charismatic. I just hope in the future that your guides will start having microphones, as it was hard to listen with loud city distractions and other tour groups…”
Chicago Loop walking donut tour with multiple bakery stops, landmark sights, and included samples for a sweet meal. Vegan options available.
“This was a great tour. Jackson was very engaging and upbeat. Made the trek through very cold weather fun. The donuts were very good. Great variety. This is not your run of the mill tour. Take it you won't be disappointed.”
See Chicago’s best sights from an open-top hop-on hop-off bus with real-time tracking, earbuds audio, and optional walking tours.
“Really enjoyed the boat trip. It was incredible and very interesting. The bus tour was fine, a great way to see the skyscrapers from within”
Deep-dish, hot dog, Italian beef and Chicago skyline stories on a small-group 4.5-hour walk with the Pedway and The Bean.
“Our tour guide was very knowledgeable and provided us with resources and facts which I appreciated. When doing another guided tour we would definitely request to have him again.”
A 3-hour Chicago Loop walk pairing deep-dish pizza and Italian beef with iconic landmarks, ending by Cloud Gate at Millennium Park.
“There’s a lot of food. Our tour took 3.5 hours, but we were stuffed by the end! But no beverages are included (at the basic rate) so consider bringing your own with you.”
1.5-hour Chicago River architecture boat tour with a local guide, stops near Navy Pier and Cloud Gate, plus drinks and snacks.
“The tour guide was awesome! Beautiful city! Very friendly & helpful crew. Would highly recommend & likely do the tour again.”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
