CHICAGO · ILLINOIS
The best of Chicago.
The 15 best 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.
Chicago Loop walking donut tour with multiple bakery stops, landmark sights, and included samples for a sweet meal. Vegan options available.
Most Popular“Nick was fabulous. Funny. Loud. Knew his donuts. The walk was easy and slow. Loved his history review too. Perfect morning tour”
Small-group Chicago architecture tour by minibus, with optional open-top river cruise. Hit the Loop, skyline views, and top icons fast.
“My family and I had the best time! Rick did such a fantastic job in showing us around Chicago and learning about the history of such a marvellous city! A 10/10 tour will definitely be coming back to do again”
Seadog speedboat from Navy Pier blasts along Lake Michigan with a live guide, skyline views, and optional Extreme Thrill spins.
“The access was very expeditious and the tour itself was so fun!”
See Chicago highlights in 2 hours on an air-conditioned minibus with live narration, key photo stops, and easy downtown pickup.
“great way to see the city, it felt like a private tour! our guide was very knowledgeable, friendly, & fun!”
A 2-hour small-group lunch cruise on Lake Michigan from Navy Pier with buffet lunch, DJ entertainment, and skyline views.
“It was not clear exactly where the ship was. I only saw 600 E Grand Avenue, we were at the pier at 11:45 for a 12:30 sailing. It took us 44 minutes to find the boat. We got there at 12:29 and just made it. I would have been extremely angry if I lost over…”
A 75-minute Seadog speedboat architecture cruise from Navy Pier. See Chicago River landmarks and Lake Michigan sights with live narration.
“Lucious was an amazing tour guide learn so many interesting things about the city and had great views and an amazing sunset”
A 3-hour Chicago bike tour for $59, riding mostly bike paths along Lake Michigan and major museums, with time for photos and stories.
“You get to see all the touristy sights. Our tour guide Dan was so knowledgeable with a great sense of humour. Beautiful scenery. Would highly recommend”
Lake Michigan lunch or dinner cruise from Navy Pier with a big buffet, live DJ, rooftop games, and skyline views. Brunch includes bottomless mimosas.
“Loved it! Atmosphere was nice and the food was good. I would suggest bringing a blazer or lightweight jacket.”
Chicago private custom city tour with hotel pickup. See Millennium Park, Loop, Lincoln Park, Hyde Park and Wrigley Field in 3–4 hours.
“This private tour is totally worth it! We had a driver and a guide take us around various parts of the city in a very spacious Landrover. Matt our guide was very knowledgeable and Harold our driver was great at maneuvering around the traffic which there was a lot of during the Memorial Day weekend.…”
Climate-controlled minibus tour of Chicago’s key architecture with three photo stops, plus optional 75-minute river cruise.
“Loved our guide Avery! Feel we learned a lot about Chicago”
A $32 small-group Chicago ghost tour through Lincoln Park, with stop-by-stop true crime and haunting stories for a spooky one-hour walk.
“Amazing tour! He was so knowledgeable about the city ghost experience I would definitely recommend :)”
A 2-hour Chicago food walk through the Loop, Riverwalk, and iconic classics, with enough tastings for a real meal and plenty of local tips.
“Allows us to sample best of local food with a local guide with history of the food explained and general history of area”
Private 2-hour downtown architecture walk from Chicago Theatre to Cloud Gate, with Pedway tunnels, river views, Picasso, and included snacks.
“Never would have known to "look up" at Macy's. We also went back to the Walnut Room for Mrs. Hering's chicken pot pie.”
City Cruises Chicago River brunch, lunch, or dinner pairs a 3-course meal with glassed-in skyline views and optional narration, DJ, and mimosas.
“The best good and service on a lunch cruise. The European style river craft was great! Views all around and up!!!”
A Chicago Lake Michigan fireworks dinner cruise with a buffet, DJ, and Navy Pier views. Smart casual, weather-dependent fireworks, great value.
“The wrong boat is listed on the confirmation email, it had the Spirit of Chicago when it was the Spirit of Navy Pier. They do not honor dress code, sport casual no gym shoes or flip flops-that’s not true because there were a plether of each. The bathrooms do not lock, I was urinating and…”
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.
