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“Great experience. Very educational but beware to bundle up. Riding on the upper level was nice but we had to go inside on the lower level a couple times to warm up.”
A historian-led Chicago Loop walk mixing Prohibition-era mob stories and reported ghost sites, with optional minibus upgrade for $52.
“Avery our tour guide was great. Highly recommend while visiting Chicago. Light walking and nice stops.”
A $49 coach tour through Chicago’s mob history with photo stops, mini museum, and story-first guides. 90–120 minutes of crime scenes.
“Great narration about mobsters. Only stop to get out of bus to see where John Dillinger was killed and Frank Nitti’s vault.”
Take a 45-minute Chicago River architecture cruise from the Magnificent Mile with live narration, top-deck views, and major landmarks.
“Great experience. Very educational on Chicago’s history and buildings. The boat ride was good as well.”
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.
“I bought a 48 hour pass and when I arrived they told me that they were closed the following day. I was not offered a refund”
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.
“Fran did an amazing job sharing her city with us! She brought us to all of the popular spots and the food was amazing.”
Join a historian-led Chicago South Loop tour blending gangster lore and ghost stories, with stops at Riverwalk, theatres, and haunted hotels.
“Great storytelling filled with fun facts that I will no doubt share with my friends to sound really smart ;)”
A 90-minute Chicago River architecture cruise with live narration, covered seating, and big skyline moments from Wrigley Building to Navy Pier.
“Great informative tour!! Wonderful history points presented, tour guide extremely knowledgeable . Great views up top!”
A 2-hour Loop walking tour focused on jaw-dropping building interiors, ending at Chicago Cultural Center, with a local guide for $35.
“Spencer gave us a great tour. It was very interesting and engaging. I highly recommend it for anyone visiting.”
Chicago Loop walking donut tour with multiple bakery stops, landmark sights, and included samples for a sweet meal. Vegan options available.
“Could not have loved this tour more! I was traveling with my 10yo and Jackson was so good to include her! Doughnuts were great too!”
See Chicago’s best sights from an open-top hop-on hop-off bus with real-time tracking, earbuds audio, and optional walking tours.
“Absolutely loved this! So informative and detailed. Lots of buses so weren't waiting long when we got off at stops. Super friendly staff. Such an enjoyable experience”
Deep-dish, hot dog, Italian beef and Chicago skyline stories on a small-group 4.5-hour walk with the Pedway and The Bean.
“Excellent Tour guide. David was so knowledgeable, patient and helpful. I was on a rolator David knew exactly where the elevators were located. By preparing for the locations, it made everyone comfortable.”
A 3-hour Chicago Loop walk pairing deep-dish pizza and Italian beef with iconic landmarks, ending by Cloud Gate at Millennium Park.
“Mike was a great tour guide and the food was amazing. The route is great because it offers such a historical lesson.”
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.
