15 Chicago Tours Worth Booking

1.Chicago Architecture River Cruise

★★★★★★★★★★5.0 · 15,756 reviews · 1 hour to 1 hour 30 minutes (approx.) · from $39Our pick

Review of Chicago’s architecture river cruise, with skyline views, expert guides, practical tips, cold-weather advice, and value details.

“Such an amazing experience! A must see while in Chicago! Tour guide was funny & knowledgeable, I did not realize there was so much history regarding the architecture of Chicago at all! I left the tour feeling so proud to be there exploring the city, that experience really fueled my fire to learn more!”

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2.Chicago River 90-Minute Architecture Tour

★★★★★★★★★★4.5 · 9,629 reviews · 1 hour 30 minutes (approx.) · from $45

Review the Chicago River 90-Minute Architecture Tour, with expert narration, skyline views, practical tips, pricing, seating, and weather advice.

“Easy Explain very well Good, the whether little cold but the boat went slow to understand everything”

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3.Chicago River: 1.5-Hour Guided Architecture Cruise

★★★★★★★★★★4.8 · 8,046 reviews · 1h 30m · from $44

See Chicago’s greatest buildings from the river on a 90-minute guided cruise with expert commentary, open decks, and climate-controlled seating.

“It was the most interesting architecture tour I have ever been!! The tour guide was very charismatic and made us laugh at lot, we explained everything in a very passionate way and we had a blast!”

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4.Gangsters and Ghosts Walking Tour

★★★★★★★★★★5.0 · 7,155 reviews · from $52

Explore Chicago’s gangster past and ghost stories on a historian-led Loop walk, with stops at the Palmer House, Riverwalk, and Congress Hotel.

“Willis was a great story teller! Easy to find, the only wish is that we were able to stop in more places. Most of the tour is just walking outside not in actual buildings.”

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5.Chicago Architecture Center River Cruise aboard First Lady

★★★★★★★★★★5.0 · 5,536 reviews · 1 hour 30 minutes (approx.) · from $57

Review of Chicago’s First Lady architecture cruise, with river views, expert docents, practical tips, pricing, and what to expect.

“Excellent tour of Chicago. Fantastic experience!! Mark was very knowledgeable and entertaining to listen to. Very friendly and organized staff. Boat was spotless and comfortable. Recommend the evening tour.”

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6.Willis Tower Skydeck and The Ledge Ticket

★★★★★★★★★★4.6 · 4,350 reviews · 45 min · from $42

Review of Chicago’s Willis Tower Skydeck and The Ledge, with practical tips on views, crowds, exhibits, timing, price, and value.

“Great experience especially when timed with the navy pier fire works”

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7.Architecture River Cruise Skip-the-Ticket Line

★★★★★★★★★★4.8 · 4,325 reviews · 1 hour - 90 minutes · from $39

Cruise all three Chicago River branches, hear stories about 40 landmarks, and see the city’s famous architecture from a fresh waterside view.

“Very nice tour with the amazing guide Joe! Thank you so much!”

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8.Chicago Crime and Mob Bus Tour

★★★★★★★★★★4.5 · 3,186 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $49

Explore Chicago mob history by coach, with Al Capone sites, the Biograph Theatre, St. Valentine's Massacre site, and Harry Caray's vault.

“Jay, our tour guide, was amazing. Very knowledgeable with a great sense of humor. We learned a lot and had a fabulous time.”

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9.360 CHICAGO Observation Deck Ticket

★★★★★★★★★★4.5 · 3,173 reviews · 30 min · from $29

Review of 360 CHICAGO, with fast elevator access, sweeping city views, CloudBar, TILT costs, timing tips, and honest value advice.

“Wow! Wow! Wow! The views from the observation deck were out of this world- almost literally. I went at sunset and got some amazing photos. Great family activity, even though I went by myself. I bought tickets at the top for The Tilt and the extra $10 was worth it. Security was quick and the elevator ride took only 40 seconds. Even if you’re scared of heights, this is worth the fear. Highly recommend!”

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10.Chicago River 45-Minute Architecture Tour from Magnificent Mile

★★★★★★★★★★4.5 · 2,924 reviews · 45 minutes (approx.) · from $28

See Chicago’s landmark architecture from the river on a 45-minute Wendella cruise with live commentary, indoor seating, and skyline views.

“A wonderful excursion to learn more about Chicago’s architectural history! Tess was an excellent guide. If it’s cold out, dress warmly!”

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11.Chicago Lake and River Architecture Tour

★★★★★★★★★★4.5 · 2,308 reviews · 1 hour 30 minutes (approx.) · from $45

Cruise Chicago’s river and Lake Michigan for skyline views, lively architecture stories, indoor seating, and practical tips before you book.

“Great outing! Worth it! Our guide was very passionate about Chicago and made the trip very enjoyable.”

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12.45-Minute Family-Friendly Architecture River Cruise

★★★★★★★★★★4.7 · 2,304 reviews · 45 min · from $28

See Chicago’s skyline from the river on a 45-minute family cruise with lively architecture stories, open-air views, and a climate-controlled cabin.

“I booked the evening tour for my anniversary. The views were beautiful in the evening. Check the weather before in case it gets cold. There is a lower deck in the event it's too cold.”

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13.Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass

★★★★★★★★★★4.0 · 2,191 reviews · 2 hours (approx.) · from $45

Big Bus Chicago review covering routes, stops, timing, weather, app tracking, audio commentary, ticket value, and who should book.

“When I booked the tour there should’ve been some kind of notice that the street were gonna been shut down and the bus operations services were ending two to three hours early due to the miracle mile light festival parade.We couldn’t get the full experience of hopping on and off because there wasn’t enough time to explore. The last stop was 3.5 miles from where we started and we had to pay for an Uber”

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14.1.5-Hour Lake and River Architecture Cruise

★★★★★★★★★★4.7 · 2,050 reviews · 1h 30m · from $44

Cruise Chicago’s river and lakefront for 90 minutes of architecture, skyline views, expert stories, and a trip through the famous Chicago Lock.

“Excellent experience! Knowledgeable, professional and interesting guide. Loved the River and Lake Michigan views. I had only done the River cruise before. Adding the lake and just seeing a smaller section of the river worked great for us. Highly recommend!”

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15.Chicago Favorites Ultimate Food and Walking Tour

★★★★★★★★★★5.0 · 1,962 reviews · 3 hours (approx.) · from $84

Chicago food tour review covering deep dish, hot dogs, Italian beef, landmarks, guide quality, price, weather, and the bike or kayak bonus.

“It's a fun and delicious way to be introduced to local food and history. We loved hearing about the architecture of famous buildings downtown. All of the food was tasty. Our tour guide was fabulous, fun, and well-informed. Highly recommend this introduction to Chicago!”

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