Best Guided tours in Chicago

Local Recommendations from our My Guide Chicago team

Explore Chicago with expert local guides offering unique insights on the city's history, culture, and attractions. Book your tour today!

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If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

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Chicago: Luxury Minibus City Sightseeing Tour

5 Reviews

Chicago: Luxury Minibus City Sightseeing Tour

Explore Chicago on a luxury minibus tour, designed for those who want to experience the city's most iconic landmarks in comfort and style. Enjoy narrated insights, scenic stops, and vibrant districts.

$65.00

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Chicago: Private Architecture Tour - 3 or 6 Hours

5 Reviews

Chicago: Private Architecture Tour - 3 or 6 Hours

Discover a city known for its architectural creativity and ingenuity. Explore some of Chicago's most iconic buildings, with the option to visit Oak Park and the homes of Frank Lloyd Wright.

$780.00

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Chicago: Historic Skyscrapers Guided Walking Tour

Explore famous buildings and architecture on a walking tour in Chicago, home to some of the world's earliest skyscrapers. See why Chicago is often called "The Birthplace of the Skyscraper."

$30.00

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Chicago: Food, History and Architecture Tour

84 Reviews

Chicago: Food, History and Architecture Tour

Discover the architecture and food scene of Chicago on a guided tour. Learn more about the prohibition era, explore the city's vibrant food scene, and taste some local well-known cuisine.

$99.00

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Chicago: Gangsters and Ghosts Luxury Minibus Tour

9 Reviews

Chicago: Gangsters and Ghosts Luxury Minibus Tour

Discover Chicago's haunted past on a luxury Gangsters & Ghosts minibus. Explore notorious crime history & hear spine-chilling tales from expert guides about the ghosts that still haunt the streets.

$65.00

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Chicago: Downtown Donut Tour with Tastings

89 Reviews

Chicago: Downtown Donut Tour with Tastings

Take a trip with Chicago's only donut tour. Making 4 stops at some of the city's best donut shops, you'll sample all the best donuts Chicago has to offer. Enjoy samples at each location and learn about the history of donuts in the windy city.

$68.00

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Chicago: First Lady River Cruise & Architecture Center Combo

22 Reviews

Chicago: First Lady River Cruise & Architecture Center Combo

Join a river cruise in Chicago featuring live certified guides and pre-recorded multilingual commentary. Book a combo that includes discounted entry to the world-famous Chicago Architecture Center.

$59.00

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Chicago: 360 CHICAGO Deck & Big Bus Hop-on Hop-off Tour

11 Reviews

Chicago: 360 CHICAGO Deck & Big Bus Hop-on Hop-off Tour

See the Windy City from a unique open-top double decker and explore the city at your own pace. Then, soak in the famous skyline from 1,000-feet high at 360 CHICAGO Observation Deck.

$80.00

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Chicago Loop Architecture Private Walking Tour

Explore Chicago's rich architectural history on a captivating tour through the historic Loop District.

$227.00

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Chicago: Oktoberfest Walking Brewery Tour in Logan Square

Learn Chicago's Brewing History One Beer at a Time! Find your new favorite beer with us in Logan Square.

$25.00

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Chicago: Gangsters & Ghosts Minibus Tour + Riverboat Cruise

Discover Chicago's haunted past on a luxury Gangsters & Ghosts minibus tour, plus a Riverboat Architecture Cruise!

$99.00

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