Chicago · TOUR REVIEWS

The 15 Best Tours in Chicago

540 tours  ·  ★★★★★★★★★★ 4.7 average  ·  from $28

A long weekend, and a city that gives you the river, the lake, the Loop and three world-class museums to fit into it. The 15 below are the bookings that earn their slot, priced and timed, with the full catalogue underneath when you want to dig deeper.

Tour Reviews

Chicago Architecture River Cruise - Getting on board at Navy Pier or Michigan Avenue
Architecture River Cruises, Architecture Tours, Cruises & Boat Tours, Tour Reviews

Chicago Architecture River Cruise

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1.Chicago Architecture River Cruise

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

See Chicago’s best buildings in about an hour with live guide commentary, pet-friendly boats, and strong value at $39.

“Such a great time!! Sam was our guide, and he was phenomenal. He told us the history of not only the buildings, but the city as a whole, and its relation to the nature it resides besides. Sam gave us historical and cultural context behind many architectural styles. He also had some great jokes. The cow puns… udderly hilarious. My friend and I are from Omaha (also called River City by locals), and we wish that our hometown had a river architectural tour like this.”

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Chicago River 90-Minute Architecture Tour - What 90 Minutes Actually Covers on the Chicago River
Architecture Tours, Tour Reviews, Tours

Chicago River 90-Minute Architecture Tour

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2.Chicago River 90-Minute Architecture Tour

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

90-minute Chicago River architecture cruise with indoor and outdoor decks, expert narration, and standout views of the skyline’s best-known buildings.

“We had a great time. The guide we had was great and explained the history and other great information along the tour. A great way to see the city and get some history too”

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Chicago River: 1.5-Hour Guided Architecture Cruise - Entering at the right dock: where to check in near the Wrigley Building area
Architecture River Cruises, Architecture Tours, Cruises & Boat Tours, Guided, Tour Reviews

Chicago River: 1.5-Hour Guided Architecture Cruise

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3.1.5-Hour Guided Architecture Cruise

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

A 90-minute Chicago River architecture cruise with expert storytelling, indoor warmth or open-air decks, and iconic skyline stops plus a cash bar.

“Our guide was first class with his knowledge and interpretation of the Chicago architecture. Combine that with the history and the ability to weave amusing anecdotes, and excellent diction made this a trip out of the ordinary.”

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Chicago: Gangsters and Ghosts Walking Tour - A Historian Guide, Clear Voices, and a Small Group That Stays Together
Gangster & Mob Tours, Ghost Tours, Tour Reviews, Tours, Walking Tours

Chicago: Gangsters and Ghosts Walking Tour

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4.Gangsters and Ghosts Walking Tour

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

Chicago Loop bootleggers, ghosts, and Al Capone lore, guided by a historian. Walk key landmarks, plus optional minibus upgrade.

“Taka was our guide and she was fantastic. We had such a good time, she was a very good story teller, loud and clear. Lots of interesting information. We learned alot and had a lot of fun.”

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Chicago Architecture Center River Cruise aboard First Lady - What the First Lady Cruise Feels Like On the Water
Architecture River Cruises, Architecture Tours, Cruises & Boat Tours, Tour Reviews

Chicago Architecture Center River Cruise aboard First Lady

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Chicago: Willis Tower Skydeck and The Ledge Ticket - Getting to S. Wacker Blvd and the lobby flow
Tickets, Tour Reviews, Willis Tower Skydeck Tickets

Chicago: Willis Tower Skydeck and The Ledge Ticket

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6.Willis Tower Skydeck and The Ledge Ticket

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

Step onto Willis Tower’s The Ledge for glass-over-city views, plus Skydeck exhibits, a film, and a timed, efficient visit.

“Awesome experience and a spectacular view of Chicago. I got the opportunity to do both this and the Chicago 360 and I feel this tower is definitely better. The staff were great too”

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Chicago: Architecture River Cruise Skip-the-Ticket Line - Live Docent Narration, Not Just Points on a Map
Architecture River Cruises, Architecture Tours, Cruises & Boat Tours, Tickets, Tour Reviews

Chicago: Architecture River Cruise Skip-the-Ticket Line

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7.Architecture River Cruise Skip-the-Ticket Line

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

Skip the ticket line for a Chicago Architecture River Cruise with live docent narration on all 3 river branches, plus a cash bar.

“This was a great tour. We went in the 8pm cruise and we were able to enjoy a beautiful sunset and then see the buildings lit up. We also got to experience some perfectly timed nighttime features, like building projections and fireworks because of the time we choose. Our guide Brian was great; entertaining and clearly loves his city. Will definitely do this again.”

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Chicago Crime and Mob Bus Tour - Price and Value: What $49 Buys You in Real Terms
Gangster & Mob Tours, Tour Reviews, Tours

Chicago Crime and Mob Bus Tour

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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

Ride Chicago by coach to the St. Valentine’s Day Massacre, Dillinger sites, and mob haunts. Live guide, photo stops, mini museum included.

“Incredibly interesting and such a cool tour!! Our tour director Maddie is a fantastic story teller and it was so cool to learn who all these people were. 2nd time in Chicago and learned more on this tour than anything else! Highly recommend!”

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Chicago: 360 CHICAGO Observation Deck Ticket - Arriving at 875 N Michigan and the skip-the-line reality
360 Chicago Observation Deck, Observation Decks, Tickets, Tour Reviews

Chicago: 360 CHICAGO Observation Deck Ticket

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9.360 CHICAGO Observation Deck Ticket

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

Skip the line for 360 CHICAGO, ride a fast elevator to the 94th-floor deck, enjoy Lake Michigan views, CloudWalk art, and upgrade TILT.

“The view!! We were lucky to have a great day to enjoy the Chicago view. No queue, so access was quick. Has to be done while in Chicago!”

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Chicago River 45-Minute Architecture Tour from Magnificent Mile - Wrigley Building, Merchandise Mart, and Lyric Opera House in Real Time
Architecture Tours, Tour Reviews, Tours

Chicago River 45-Minute Architecture Tour from Magnificent Mile

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

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

A 45-minute Chicago River architecture cruise from the Magnificent Mile, with live narration, great views, and indoor warmth options.

“This was such a fun experience even in the freezing cold! I went solo and didn’t feel out of place. The directions were clear, the tour started on time with plenty of seating and options for alcoholic/non alcoholic beverages. Great information and stunning views along the river 10/10”

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Chicago Lake and River Architecture Tour - Chicago River highlights: locks, skyline layers, and the on-the-hour fountain
Architecture River Cruises, Architecture Tours, Lake Michigan Cruises, Tour Reviews, Tours

Chicago Lake and River Architecture Tour

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11.Chicago Lake and River Architecture Tour

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

A 1.5-hour Chicago architecture cruise with live narration, Lake Michigan skyline views, and river landmarks from Wendella.

“This was a great tour if you are wanting to many of the buildings and the skyline from the lake. The guide was knowledgeable with the history and construction of the buildings”

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Chicago: 45-Minute Family-Friendly Architecture River Cruise - Your Boarding Day: Finding 400 N Michigan Ave and Settling In
Architecture River Cruises, Architecture Tours, Cruises & Boat Tours, Tour Reviews

Chicago: 45-Minute Family-Friendly Architecture River Cruise

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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass - The 11 Stops That Shape Your Chicago Day
Hop-On Hop-Off Bus Tours, Tour Reviews, Tours

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

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Chicago: 1.5-Hour Lake and River Architecture Cruise - Wrigley to Wolf Point: How the Buildings Tell Time
Architecture River Cruises, Architecture Tours, Cruises & Boat Tours, Lake Michigan Cruises, Tour Reviews

Chicago: 1.5-Hour Lake and River Architecture Cruise

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Chicago Favorites Ultimate Food and Walking Tour - Your food lineup: what you’ll eat, and what changes by AM or PM
Food, Food & Drink, Tour Reviews, Tours, Walking Tours

Chicago Favorites Ultimate Food and Walking Tour

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15.Chicago Favorites Ultimate Food and Walking Tour

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

Chicago’s classic foods meet downtown landmarks on an easy 3-hour walk, with tastings included and a free bike or kayak bonus.

“The tour guide was great and since we were charged the entire fee but didn’t get to see everything without warning that booking on New Year’s Day tour one tour stop food place would be canceled. That was disappointing. But you all can use that extra we didn’t use for that place and give to our tour guide lady as her tip. She was with Gabe from Bobby bike and hike tours 11:30 tour on 1.1.2026. She was trying to be as enthusiastic and did explain as much about Chicago but we just wanted to go sit down and eat at places :) And they were nice places to stop…”

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New in Tour Reviews

★ 5.0Chicago Private Boat Rental – Explore Chicago’s Skyline & WatersFrom $2,2751 reviews
★ 1.0Chicago Christmas Loop Tour1 reviews
★ 5.0Wicker Park Walking Tour History Trivia and Local FlavorsFrom $401 reviews
★ 4.0Up to 36% Off The Immersive Messi Experience ChicagoFrom $391 reviews
Chicago All Day Water TaxiFrom $331 reviews
★ 5.05-Day Tour of Superior, Huron and Michigan from ChicagoFrom $1,3151 reviews
★ 2.0Glow and Glide Paddleboard Sunset Experience Chicago1 reviews
★ 5.0Yucatan Delights by a Michelin Star-Trained Chef in ChicagoFrom $2051 reviews
★ 5.0Private Bear Painting Class in ChicagoFrom $931 reviews
★ 5.0Chicago Mystery Scavenger Hunt: Solve the Loop’s 1920s WhodunitFrom $231 reviews
★ 1.0Chicago Gangsters Tour – Colorful History and Dark PastFrom $991 reviews
★ 5.0Downtown Chicago Guided Walking Tour Semi-Private 12ppl MaxFrom $511 reviews
★ 5.0Wizard of Oz Movie Tour in ChicagoFrom $01 reviews
★ 1.0The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour1 reviews
★ 3.04 Day Tour from Chicago: Detroit Toledo Buffalo and Niagara FallsFrom $1,3361 reviews

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Architecture River Cruises24Lake Michigan Cruises36Gangster & Mob Tours28Pizza Tours10Walking Tours111Museums23
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