Chicago · CITY TOURS
24 reviewed
This is the shortlist we would hand a friend: the 15 city tours worth booking in Chicago, each with its price, its verdict, and the one thing to know before you commit.
Taste Chicago’s Loop donuts on a 2-hour walking tour. All samples included, vegan options available, guided city sights and laughs.
“My kid and I loved this. Our guide, Lauren, was super patient and knowledgeable. We ate so much and had a great time. Come starving!”
A small-group Chicago minibus tour with skyline stops and an optional Chicago River architecture cruise. Fast, easy, and built for first-timers.
“Chicago Bob was exceptional with the amount of information he had to share. Excellent, non-stop commentary. All of us enjoyed it immensely.”
Zip Chicago’s lakefront in a 2,000-hp speedboat, learn architecture and skyline stories, and choose the Extreme Thrill for 360° spins.
“Such a fun ride! Jake, our host was very funny and had great energy! Great family ride!”
See Chicago’s biggest highlights in 2 hours on a small, air-conditioned minibus with live narration, Bean-area drop-off, and key photo stops.
“It is fun and very intimate. It’s a great way to learn about the city. It takes you to many cool spots.”
Small-group Lake Michigan lunch cruise from Navy Pier with a chef-prepared buffet, DJ and games, plus skyline views in about 2 hours.
“My wife and I enjoyed the experience. Food was really good and buffet style. Service was attentive and bar access was good.”
Enjoy a 3-course plated lunch or dinner on Lake Michigan with 360° Chicago skyline views, a live DJ, and dance time.
“Food could’ve been a little warmer. The taste of the food was good. The bathroom had an odor. My birthday was celebrated on the cruise, I parted to the beautiful music and the DJ was great!”
75-minute Seadog speedboat architecture cruise from Navy Pier with live guide narration, Harbor Locks, Chicago River landmarks, and Lake Michigan speed.
“This boat ride was lots of fun and very informative! Our guide, Andrew, was knowledgeable and very funny! This was the best way to see Chicago.”
Ride Chicago’s lakefront and museum campus on mostly car-free bike paths, hitting iconic parks, art, and major sights in 3 hours.
“Bike trip was lots of fun, tour guide was great and made the trip worthwhile. It rained part way through our trip but the guide had ponchos for everyone!”
City Cruises Chicago Lake Michigan lunch, dinner, or brunch with 360° skyline views, DJ, games, and a buffet plus mimosas on brunch.
“Note: Meeting place is at the pier where your boat is docked not in Navy pier address (entrance). All in all it was an excellent activity. The staff was excellent!”
Private Chicago tour with hotel pickup. See Millennium Park, The Loop, Lincoln Park, Hyde Park, and Wrigley Field in 3–4 hours.
“Everything we wanted and more. Our expectations were exceeded. I would highly recommend this tour with TJ and our tour guide!!!”
Chicago highlights by climate-controlled minibus plus optional 75-minute river architecture cruise, with photo stops and expert English guiding from $48.
“Rick was a delight and he really knew his history of Chicago!”
2-hour City Cruises Chicago river dining cruise with a chef-made 3-course meal, glass-enclosed views, and architecture narration on daytime sails.
“The best good and service on a lunch cruise. The European style river craft was great! Views all around and up!!!”
A small-group 1-hour ghost walk in Lincoln Park, linking haunted parks, an asylum building, Tudor pubs, and old theaters. From $32.
“Tour guide was sweet, but tour itself was lacking content. They need to add more concrete stories to really enrich the tour.”
A 2-hour Chicago food tour hitting the Loop and Riverwalk for a full-meal worth of iconic eats plus city stories, in a small group.
“Dash is a true Chicago native who loves his town and knows so much about the city. He gave us a ton of information and we enjoyed the food tastings as well.”
2-hour private Chicago architecture walk from the Chicago Theatre to Cloud Gate, with Pedway access, tastings, and insider stories.
“Great walking tour, learnt many facts & tasted some local treats. Rich was a great guide, we were even treated to his rendition of a couple of songs & some music to walk the Pedway!!! Highly recommend”
