USA · CHICAGO TOURS

15 Chicago Tours That Repay the Ticket

73 tours  ·  from $24

The good chicago tours fill weeks ahead and the best ones go first. Below: the 15 to book early, what each includes and where they differ.

Chicago Architecture River Cruise - What you see along the river
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Chicago Architecture River Cruise

1.Chicago Architecture River Cruise

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

Cruise the Chicago River for about 60 to 90 minutes while an expert guide explains Chicago’s buildings, engineering, and Great Fire of 1871. You’ll pass the Wrigley Building, Tribune Tower, John Hancock Center, Willis Tower, Marina City, and Aqua. Boats have restrooms and a full bar, and dogs are welcome.

“Wonderful excursion with a highly knowledgeable guide. Jim was a terrific guide with real passion for Chicago. His tour alone would make you want to come back.”

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Chicago River 90-Minute Architecture Tour - Choose your seat before the skyline begins
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Chicago River 90-Minute Architecture Tour

2.Chicago River 90-Minute Architecture Tour

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

Board Wendella near the Wrigley Building for a 90-minute cruise through all three branches of the Chicago River. An expert guide explains more than 130 years of Chicago architecture as you pass Marina City, Willis Tower, the Merchandise Mart, the Riverwalk, and the Lyric Opera. Choose indoor climate-controlled seating or an open-air deck.

“Appropriate time. Great tour guide. She knew the area, had nice humor and voice. Liked that we came during the day to experience the varied character on buildings”

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Chicago River: 1.5-Hour Guided Architecture Cruise - The main branch, from Wrigley to Wolf Point
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Chicago River: 1.5-Hour Guided Architecture Cruise

3.Chicago River: 1.5-Hour Guided Architecture Cruise

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

Spend 90 minutes with guides such as John, Sarah, Alex, or Scotty D, cruising from Michigan Avenue through Chicago’s main, north, and south river branches. You’ll see Marina City, Willis Tower, the Merchandise Mart, and modern landmarks from an open deck or climate-controlled cabin, with a cash bar serving local drinks and Garrett’s Popcorn.

“Unreal tour guide, super knowledgeable. Stunning views, great day out.”

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Chicago: Gangsters and Ghosts Walking Tour - Meeting near Wacker Drive and starting in the Loop
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Chicago: Gangsters and Ghosts Walking Tour

4.Gangsters and Ghosts Walking Tour

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

Walk about 1.5 miles through Chicago’s Loop with a historian guide, hearing true crime stories, ghost accounts, and tales of Al Capone. Stops include Millennium Park, the Palmer House, the Riverwalk, the Chicago Theatre, and the Congress Plaza Hotel. Guides such as Taka, Sophia, Tanner, and Avery are known for clear delivery and strong storytelling.

“Taka, with her passionate love of history, gave us a fascinating introduction to the history of Chicago. She switched easily from Al Capone and gang warfare of the prohibition era and then told of tragic loss life on the SS Eastland. So many great stories, we loved it!”

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Chicago Architecture Center River Cruise aboard First Lady - What the 90 minutes actually covers
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Chicago Architecture Center River Cruise aboard First Lady

5.Chicago Architecture Center River Cruise aboard First Lady

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

Cruise the Chicago River aboard Chicago’s First Lady for 90 minutes of architecture and city history. A Chicago Architecture Center docent, such as Cynthia, Laura, Amy, or Mark, explains landmarks including Marina City, Willis Tower, Navy Pier, and 150 North Riverside. Choose an open-air seat or the climate-controlled lower salon, with a full bar onboard.

“I’m really glad I took the tour. It’s a great way to spend 90 minutes if you want to learn more about Chicago during a short trip. The guide was fantastic, she knew so much about Chicago’s history, especially the river, the bridges, and the buildings. The bar was great too: warm and cosy, and a perfect place to enjoy a couple of beers with friends. You won’t regret it.”

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Chicago: Willis Tower Skydeck and The Ledge Ticket - Chicago’s story comes before the elevator
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Chicago: Willis Tower Skydeck and The Ledge Ticket

6.Willis Tower Skydeck and The Ledge Ticket

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

Visit Skydeck Chicago on the 103rd floor of Willis Tower, explore exhibits on Chicago’s past and architecture, then step onto The Ledge, a glass balcony extending 4.3 feet beyond the building. Your timed ticket includes the Skydeck app and access to the theater presentation. A Fast Pass option adds quicker elevator and Ledge access.

“excellent time at the Willis tower, the ledge is worth the little extra as a great experience. preferred it to the 360 tower”

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Chicago: Architecture River Cruise Skip-the-Ticket Line - Boarding with a skip-the-ticket-line ticket
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Chicago: Architecture River Cruise Skip-the-Ticket Line

7.Architecture River Cruise Skip-the-Ticket Line

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

Board Shoreline Sightseeing for a live, English or Spanish narrated cruise past about 40 Chicago landmarks. Guides such as Chicago Bob, Jeremy, Juan, and Kevin mix architecture, local history, and humor. The cruise lasts 75 minutes in warm months and 60 minutes from November 1 to April 15, with a cash bar on most boats.

“The tour leader was very knowledgeable about the history of Chicago from a waterfront viewpoint. He had the audience entertained as the we caught the beautiful sunset. This tour is a MUST.”

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Chicago Crime and Mob Bus Tour - The Biograph Theatre and John Dillinger’s final hours
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Chicago Crime and Mob Bus Tour

8.Chicago Crime and Mob Bus Tour

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

Ride a climate-controlled coach through Chicago’s crime landmarks with guides such as Jay, Dane, Jamie, Sophia, or Maddie. You’ll hear stories of Al Capone, John Dillinger, Bugs Moran, and Frank Nitti, stop at the Biograph Theatre and Harry Caray’s mini mob museum, and visit historic crime scenes. The 90-minute to two-hour tour costs $49.

“the tour is about mafia and talk more about jhon dillinger a bank robber and mc Donald selling crak then AL CAPONE the tour don't talk about capone the real gangster i specs to see the places he live or operate this tour is not good and expensive .”

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Chicago: 360 CHICAGO Observation Deck Ticket - The 40-second ride to the 94th floor
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Chicago: 360 CHICAGO Observation Deck Ticket

9.360 CHICAGO Observation Deck Ticket

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

Ride one of North America’s fastest elevators to the 94th floor of 875 N. Michigan for wide views of Chicago, Lake Michigan, and four states. Explore the lower concourse exhibits, walk through CloudWalk, relax at CloudBar, and use the Magnicity app for extra stories. TILT is optional and costs extra on site.

“great views of the city, plenty of time to look around and take photos”

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Chicago River 45-Minute Architecture Tour from Magnificent Mile - Finding the dock at 400 N Michigan Avenue
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Chicago River 45-Minute Architecture Tour from Magnificent Mile

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

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

Set out from the Wrigley Building on a 45-minute Wendella cruise through Chicago’s main river channel and part of the south branch. Hear live stories from guides such as Tess, Zach, Chris, and Alyssa while viewing the Riverwalk, Michigan Avenue Bridge, Wrigley Building, Merchandise Mart, Lyric Opera, Marina City, and Willis Tower. Choose an open deck or climate-controlled lounge.

“Be prepared to gawk! The views were stunning and the information was knowledgeable. Would recommend!”

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Chicago Lake and River Architecture Tour - The Chicago River: close views and big city stories
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Chicago Lake and River Architecture Tour

11.Chicago Lake and River Architecture Tour

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

Cruise from Wendella’s Michigan Avenue dock along the Chicago River and Lake Michigan for 90 minutes of architecture stories and skyline views. Guides such as John, Kenny, Lucas, and Tess bring humor to the history. Arrive early for first-choice seating, and bring a jacket for the windy lake portion.

“Our tour guide Lucas was great!! Our family and friends from Toronto Canada really enjoyed it! Great experience!”

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Chicago: 45-Minute Family-Friendly Architecture River Cruise - Starting near the Wrigley Building
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Chicago: 45-Minute Family-Friendly Architecture River Cruise

12.45-Minute Family-Friendly Architecture River Cruise

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

Cruise the Chicago River from Lake Shore Drive toward Willis Tower and back with a lively English-speaking guide. You’ll have indoor and outdoor decks, climate-controlled seating, skyline photo spots, and a cash bar with local beer and spirits. Guides such as Kenny, Zach, and Alyssa keep the architecture talk fun for adults and children.

“Well managed, knowledgeable and witty guide, comfortable ride, value for money”

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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass - Stops 5 and 6: Adler Planetarium and Museum Campus
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Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass

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

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

Use a 24, 48, or 72-hour Big Bus Chicago pass to circle downtown sights including Millennium Park, Navy Pier, Grant Park, and the Magnificent Mile. Ride the open-top deck for clear city views, or use the enclosed lower deck in poor weather. The app shows stops and bus locations, while digital commentary covers Chicago’s landmarks.

“My husband and I enjoyed the big bus tour. It was very convenient in the winter with the snow. The bus was covered so you were protected from the cold and wind. Also they provided headphones so you could listen to the audio tour.”

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Chicago: 1.5-Hour Lake and River Architecture Cruise - Starting near the DuSable Bridge
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Chicago: 1.5-Hour Lake and River Architecture Cruise

14.1.5-Hour Lake and River Architecture Cruise

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

See Chicago from two angles on a 90-minute cruise led by guides such as Lucas, Kenny, Jack, and Sarah. Travel from the DuSable Bridge to Wolf Point, pass through the Chicago Lock, then head onto Lake Michigan for wide skyline views, Navy Pier, Grant Park, and the city’s great towers.

“This was an outstanding tour and I learned a lot about Chicago, a city I grew up by. The architecture as fascinating. I definitely recommend taking the combined river/lake tour. I do recommend that literature about the tour provide recommendations for parking.”

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Chicago Favorites Ultimate Food and Walking Tour - Start with deep dish at Lou Malnati’s or Gino’s East
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Chicago Favorites Ultimate Food and Walking Tour

15.Chicago Favorites Ultimate Food and Walking Tour

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

Walk about 1.5 miles through Chicago’s Loop with an English-speaking guide such as Gabe, Fran, Jessika, or Kevin. Taste deep-dish pizza, a Chicago hot dog, Italian beef, Garrett popcorn, and a brownie or gelato. The $84.99 tour also includes a two-hour bike or kayak rental, with seasonal limits.

“The food walking tour was awesome! Our tour guide, Gabe, was fantastic! He was very informative and a great person to show us around a small part of the city. I wasn't sure if this tour would include enough food, but I was so wrong! At the end of the tour, my wife and I were both stuffed! The food at all of our stops was really good. Nothing that blows your mind away, but all really tasty and fresh! Lots of walking, lots of food and lots of great facts/stories about Chicago.”

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New in Chicago Tours

★ 5.0BYOB Spray Paint and Sip at Studio W.I.P.From $45401 reviews
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★ 5.0Bikes, Bites & Views: Chicago’s Signature Dishes Bike Tour-AdultsFrom $89732 reviews
★ 4.0City Cruises Chicago: Signature Lunch Cruise on Lake MichiganFrom $66348 reviews
★ 4.5Field Museum of Natural History Admission TicketsFrom $29489 reviews
★ 5.0Chicago Loop District Food Tour with Deep Dish & Beef SandwichFrom $84870 reviews
★ 4.5Chicago Sightseeing River and Lake CruiseFrom $45509 reviews
★ 5.0Skip-the-line: Art Institute of Chicago Guided TourFrom $71417 reviews
★ 5.0Chicago Architecture Tour: Underground Pedway and the LoopFrom $35388 reviews
★ 3.5Museum of Ice Cream Chicago Admission TicketFrom $43396 reviews
★ 5.0Medieval Torture Museum Ticket with Audio Guide and Ghost HuntingFrom $35962 reviews
★ 4.5Lake Michigan Skyline Cruise in ChicagoFrom $32897 reviews
★ 5.0Chicago Gangster and Food Walking TourFrom $79471 reviews
★ 5.0Flyover in ChicagoFrom $38486 reviews
★ 5.0Chicago’s Secret Interiors Architectural Walking TourFrom $35635 reviews

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