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Chicago Downtown Highlights Private Walking Tour

ExperiencesToursGuided toursNeighborhood toursOutdoor activitiesCulture & historyLandmarks & monumentsSightseeingPrivate tours

Explore the vibrant city of Chicago on a private walking tour led by a knowledgeable local guide

$413.00

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Chicago: 1.5-Hour Scenic Sunset Lake Cruise

738 Reviews

ExperiencesWater activitiesOutdoor activitiesNature & adventureActivities for couplesToursGuided toursHidden gemsSightseeingViewing pointsCruises & boat toursSunset toursFood & drinks

Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. Toast the end of the day with a glass of wine, ice-cold beer or hand-crafted cocktail.

$45.00

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Chicago River 90-Min Architecture Boat Tour

24 Reviews

ExperiencesSightseeing on wheelsCulture & historyDay tripsGuided toursLandmarks & monumentsToursArtDay Trips FromWater activitiesCruises & boat toursSightseeingArchitectureEducational activities

Take a guided Chicago Architecture River Tour. Cruise past landmarks, learn history, see future projects, and enjoy stops at Navy Pier and Goose Island. A unique look at Chicago’s skyline awaits!

$32.00

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Chicago Walk: Prohibition, Architecture & Hidden Gems

93 Reviews

ExperiencesNeighborhood toursLandmarks & monumentsCulture & historyGuided toursToursSightseeingEducational activitiesPrivate toursArchitecture

Explore Chicago’s streets on foot and uncover the legacy of the Prohibition Era. See iconic sights, stunning architecture, and learn how history, crime, and design shaped the city we know today.

$49.00

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Chicago: Lakefront Neighborhoods Bike Tour

123 Reviews

ExperiencesNature & adventureOutdoor sportsGuided toursSightseeing on wheelsOutdoor activitiesNeighborhood toursToursHidden gemsBike toursSightseeingGarden & park tours

Join this guided bike tour of Chicago neighborhoods, parks, and beaches. Pass by the opulent lakeside neighborhoods, Old Town historic district, and North Avenue Beach.

$59.99

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Chicago: Private Architecture Tour - 3 or 6 Hours

7 Reviews

ExperiencesWheelchair accessibleLandmarks & monumentsArtCulture & historyGuided toursToursPhotography toursPrivate toursSightseeingArchitecture

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: Food and Culture Walking Tour

7 Reviews

ExperiencesToursNeighborhood toursGuided toursCulture & historyHidden gemsFood & drinks

Savor the iconic flavors of Chicago, like deep-dish pizza and Italian beef, as you learn about its history, legends, and more from a local. Come hungry!

$39.00

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The Best of Chicago in 2H Walking Tour

1 Reviews

ExperiencesLandmarks & monumentsToursCulture & historyNeighborhood toursOutdoor activitiesGuided toursWheelchair accessibleArchitectureSightseeingPrivate tours

Explore the best of Chicago's downtown in a 2 hours walking tour with a fun local guide, this area is famous for its bold architecture, museums and landmarks such as the Cloud Gate and the Riverwalk.

$40.00

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Chicago: Private 3-Hour Al Capone Gangster Tour

9 Reviews

ExperiencesTV & movie toursGuided toursCelebritiesToursWheelchair accessibleCulture & historySightseeingPrivate tours

Visit the notorious hangouts of John Dillinger, the Untouchables, and Al Capone with an expert historian as your guide. Chicago’s mob history has long been immortalized in popular media - embark on this Chicago gangster tour to learn the true story.

$880.00

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Chicago: Full-Day Guided City Tour by Bus

ExperiencesToursGuided toursSightseeing on wheelsDay Trips FromLandmarks & monumentsDay tripsCulture & historyPrivate toursSightseeing

Discover the best of Chicago on a full-day city tour with a local guide. See the city's top sights, including Millennium Park and Michigan Avenue, and customize your experience with optional tickets.

$122.00

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Chicago Walking Tour: See Inside Art Deco Masterpieces

7 Reviews

ExperiencesLandmarks & monumentsCulture & historyArtGuided toursNeighborhood toursToursMuseums & exhibitionsSightseeingArchitecture

Experience the elegance, glam, and glitz of the 1920s on this 2-hour walking tour of downtown Chicago! Most tours walk right by these stunning masterpieces without ever going inside -- but we do!

$35.00

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