CHICAGO · ILLINOIS
The best of Chicago.
The 15 best sightseeing & city tours in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
Take a 45-minute Chicago River architecture cruise from the Magnificent Mile with live narration, top-deck views, and major landmarks.
Most Popular“Chris was so much fun! He was very informative ! My friends and I booked this experience during the freezing cold and he was such a trooper ! We had so much fun !”
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.
“The operator canceled the days trip and never notified us or any one else. It was difficult to contact the operator via phone or emails”
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.
“Great city tour! Chicago Dave was awesome and full Of information, it was fun and easy! Would highly recommend. Learned a lot about Chicago!”
Small-group Chicago architecture tour by minibus, with optional open-top river cruise. Hit the Loop, skyline views, and top icons fast.
“It was fabulous. The tour guides were amazing and fun carefree way to learn about the city. Will do it again”
See Chicago highlights in 2 hours on an air-conditioned minibus with live narration, key photo stops, and easy downtown pickup.
“Our guide, Rick was knowledgeable and funny, and he kept our needs in mind! It was a great way to see the city for the first time.”
Cruise Chicago’s Chicago River and Lake Michigan in about 90 minutes, with live narration and great skyline photos for one fair price.
“It was amazing to hear about Chicago. It was my visit and can't wait to return. We stay downtown Chicago and it was beautiful.”
Fully narrated Chicago River and Lake Michigan cruise with skyline views, a real harbor lock pass, and family-friendly fun for about 90 minutes.
“Greatly enjoyed the trip...and I'm a Chicagoan born & raised. We had perfect weather so that made it all the better.”
Chicago private custom city tour with hotel pickup. See Millennium Park, Loop, Lincoln Park, Hyde Park and Wrigley Field in 3–4 hours.
“The knowledge of Mike was simply outstanding !! TJ and Mike are a great team , my wife and I had plenty of laughs but also we learnt so much about the history of the city.”
Climate-controlled minibus tour of Chicago’s key architecture with three photo stops, plus optional 75-minute river cruise.
“Th guide was super nice, friendly and knowledgeable. I liked seeing the various neighborhoods and learning about Chicago.”
A 90-minute small-group RHIB cruise in Chicago with Captain Ken, life jackets, lakefront speed, and skyline views near Navy Pier.
“I enjoyed the experience. It was very informative. I would recommend that you wear a sweater or jacket because of the winds during the ride.”
Private 2-hour downtown architecture walk from Chicago Theatre to Cloud Gate, with Pedway tunnels, river views, Picasso, and included snacks.
“Dave was so knowledgeable about the history of the city. It was informative and fascinating and he is a great you’re guide”
A 5-hour small-group Chicago tour mixing Prohibition-era architecture and classic food tastings, ending at Millennium Park and the Bean.
“Great tour, highly recommended! Dave was a thoroughly engaging, and knowledgeable guide who clearly has a passion for history and architecture. My only recommendation is to include the food stops earlier in the tour since it's unlikely that guests have eaten lunch prior to a 1 PM food/architecture tour.”
Walk Michigan Avenue’s landmarks and architecture on a 2-hour guided tour, with optional 360 Chicago skyline views from 1,030 feet.
“Excellent tour with Ben. Better than expected. He was knowledgeable, informative and very entertaining. We covered a lot of ground and it was a wonderful mix of history, architectural sites , beautiful landmarks and holiday decor. Highly recommend.”
Ride Chicago’s L for a short, photo-friendly loop with architecture stops, CAC galleries, and train fare included in a small group.
“Tour and guide was excellent. Far exceeded my expectations. My guide was very knowledgeable and eagerly shared his knowledge and experience with the group eagerly answering all questions.”
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.
