15 Guided Tours in Chicago Worth Booking

1.1.5-Hour Guided Architecture Cruise

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

Cruise Chicago’s main river and both branches for 90 minutes with a live English-speaking guide. You’ll see Marina City, Willis Tower, the Wrigley Building, Aqua, and more, while choosing open-air or climate-controlled seating. Guides such as John, Sarah, Alex, and Scotty D bring humor and solid city context.

“We had a blast. I first did this cruise back in May with my 81 year old dad. Loved it so much that on my return visit to Chicago I brought 11 of my family memebers. So great!”

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2.Gangsters and Ghosts Guided Walking Tour

★★★★★★★★★★4.7 · 1,697 reviews · 2 hours · from $36

Spend two hours with an English-speaking historian guide such as Max, Baylor, Tanner, or Sophia, tracing Chicago’s gangster past and ghostly legends. Walk about 1.5 miles through the South Loop, visit Palmer House and Congress Hotel, and pause at a former gangster hangout.

“Great! Even in cold winter the walk was very enjoyable. Our guide Max was also very attentive and cheerful; We will ask for her again in our next visit soon. Hopefully not so cold!”

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3.Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

★★★★★★★★★★5.0 · 962 reviews · 1 hour 30 minutes (approx.) · from $35Top rated

Walk through Chicago’s 6,000-square-foot Medieval Torture Museum at your own pace. Your ticket includes a mobile audio guide and ghost-hunting app, with hundreds of torture, restraint, interrogation, and execution displays. Expect dim lighting, realistic wax figures, hands-on exhibits, and a decidedly adult atmosphere.

“It was an eye-opening experience to see some of the gruesome torture devices! Crazy that these things were actually used on people in midieval times.”

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4.2-Hour Guided Segway Tour of Chicago

★★★★★★★★★★5.0 · 442 reviews · from $65

Learn to ride a Segway, then follow a guide such as Mike Artur through Grant Park, Buckingham Fountain, Museum Campus, and the lakefront. Some departures use a Riverwalk route past Navy Pier, Michigan Avenue, Millennium Park, and Chicago’s famous bridges. Groups are limited to eight.

“If you want to explore the "museum campus" this is the tour for you, if you except a tour of the city then you will be disappointed. The description states 2 hour "Tour of Chicago". it was barely 1.5 hours, and we only toured the campus which we had already done the day bRead more”

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5.Skip-the-line: Art Institute of Chicago Guided Tour

★★★★★★★★★★5.0 · 417 reviews · 2 hours 30 minutes (approx.) · from $71

Join guides such as Joel, Bernie, Scout, or Colleen for a fast, story-filled tour of the Art Institute of Chicago. You’ll see famous works by Van Gogh, Seurat, Hopper, Picasso, and O’Keeffe, with admission included and a group capped at 12.

“So many good things to say! We learned about art through the stories of the artists.. so interesting! Joel is passionate about art and so personable!”

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6.Private Art Institute of Chicago Skip-the-Line Guided Tour

★★★★★★★★★★5.0 · 275 reviews · 2 hours 30 minutes (approx.) · from $85

Spend about 2.5 hours with an English-speaking guide such as Heath, Spiro, Samantha, or Mandy, touring the Art Institute’s major works and lesser-known rooms. Your ticket is included, the route can follow your interests, and the museum is wheelchair friendly.

“Heath was masterful! Weaving together hundreds of years of art history with culture, some politics, and a little self-reflection. From details about artists lives, to changes in popular culture, to specifics of paintings and everything in between and around them, Heath delivered a captivating and exciting trip through the Institute.”

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7.Guided Sunset Cocktail & Architecture Tour

★★★★★★★★★★4.6 · 203 reviews · 1h 30m · from $68

Cruise the Chicago River for 90 minutes with an English-speaking guide, a cocktail or soft drink, and views of more than 50 buildings. You will pass under old bascule bridges as daylight fades and downtown lights come on. A teacher-guide may lead the tour, with drinks and snacks available on board.

“The guide was very engaging and informative. Lots of fun - bartenders were also great and very speedy for how many people they had to serve”

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8.Big Bus Chicago: Sunset Tour by Open-Top Bus with Live Guide

★★★★★★★★★★4.0 · 165 reviews · from $49

Ride an open-top double-decker bus through Chicago at sunset, passing Navy Pier, the Magnificent Mile, Millennium Park, the Wrigley Building, and the Museum Campus. A live English or Spanish guide provides the stories, with guides such as Matty and Bernie praised for humor and city knowledge.

“Bug bus broke before we left We had to cancel. Big bus should have another bus to replace it and have the excursion, not cancel it.”

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9.1.5-Hour Guided Architecture Riverboat Tour

★★★★★★★★★★4.7 · 93 reviews · 1h 30m · from $57

Cruise the Chicago River for 90 minutes aboard a classic 200-passenger boat while a live English-speaking docent explains more than 50 landmark buildings. Guides such as Jim and Ed bring history and humor, while free coffee, lemonade, soft drinks, and snacks make the ride easy to enjoy.

“I really just enjoyed the ride looking at all the buildings. Our guide had a passion for architecture and history which enhanced the tour. I think the only problem was finding the cruise itself. Just around the corner from the cruise was a souvenir shop. Score”

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10.Art Institute of Chicago Private Expert Guided Tour

★★★★★★★★★★5.0 · 84 reviews · 2 hours (approx.) · from $215

Spend about two hours with a private English-speaking guide at the Art Institute of Chicago. Ask for favorite works, focus on artists such as Van Gogh or Hopper, and see major pieces including Nighthawks, American Gothic, and Seurat’s La Grande Jatte.

“Joe was an amazing guide. Informative and very interesting! Explained the history of the artist as well as the painting.”

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11.Downtown Chicago TV and Movie Sites Guided Walking Tour

★★★★★★★★★★4.5 · 23 reviews · 2 hours (approx.) · from $44

Join an English-speaking guide at 10:00 am for a two-hour walk through downtown Chicago’s movie and TV locations. You’ll see sites linked to Ferris Bueller’s Day Off, Public Enemies, Ocean’s 11, and The Dark Knight, with guide Dan among the possible hosts.

“Excellent insight to film locations and movie and tv shows past and present . Great tour would recommend.”

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12.Chicago Self-Guided Audio Tour

★★★★★★★★★★4.0 · 9 reviews · 3 to 9 hours (approx.) · from $6Best value

Use private SoundCloud and Google My Maps links to explore 15 Chicago sights at your own pace. Short English audio segments cover architecture, art, science, and local history. Start anywhere, skip stops, and spread the experience across up to six days, with admission fees paid separately.

“Very informative and interesting. The guide spoke articulately and loud enough for everyone to hear and he had interesting forklore and stories.”

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13.Chicago’s Gold Coast Hidden History: A Self-Guided Audio Walk

★★★★★★★★★★4.5 · 7 reviews · 50 minutes (approx.) · from $7

Follow a local historian through Chicago’s Gold Coast with the VoiceMap app. This self-guided walk links the Chicago History Museum, International Museum of Surgical Science, Three Arts Building, historic mansions, and Zebra Lounge. Offline maps and lifetime access let you walk at your own pace.

“Tour was informative. The use of visitor was klunky. Had to order the tour twice to use. Viator has committed refund one of the unneeded purchases. Walk and auto play needs some work. Price was right.”

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14.Chicago Riverwalk Self-Guided Walking Tour

★★★★★★★★★★4.0 · 6 reviews · 1 to 2 hours (approx.) · from $14

Explore Chicago’s riverfront with a GPS-guided audio tour covering the Wrigley Building, DuSable Bridge, Marina Towers, Merchandise Mart, Tribune Tower, and more. You listen at your own pace, use offline maps, pause for photos, and return to the tour on future trips with lifetime access.

“Overall a great review of Chicago's history and architecture! The walk along the river is very enjoyable!”

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15.Chicago Millennium Park Self-Guided Walking Tour

★★★★★★★★★★4.5 · 5 reviews · 1 to 2 hours (approx.) · from $14

Use the Action Tour Guide app for a self-guided walk through Millennium Park. Hear stories about Cloud Gate, Crown Fountain, Pritzker Pavilion, Lurie Garden, and Nichols Bridgeway while moving at your own pace, with offline access and lifetime use.

“Self paced walking tour so we could stop & listen, check side info. or just stop for a hot dog and lemonade between spots. Only complaint is when it says only run the tour, it really is only the tour. The couple times I toggled over to take a photo it stopped & I had to re-start it. No big deal, it picked up with where we were.”

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