Page 2 - Outdoor activities in Chicago

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Chicago: Lakefront Neighborhoods Bike Tour

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: Best of Attractions Walking Tour +Bike/Kayak Rental

5 Reviews

ExperiencesLandmarks & monumentsCulture & historyNeighborhood toursOutdoor activitiesWheelchair accessibleToursDay Trips FromDay tripsGuided toursSightseeingGarden & park toursPrivate tours

Explore Chicago's best with a guided tour covering Millennium Park, Riverwalk, Michigan Ave, the Chicago Theater, and more. Maximize your experience with a complimentary 2-hour bike or kayak rental.

$44.99

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2 Hour Chicago Pier Fireworks & Evening Segway Tour

7 Reviews

ExperiencesOutdoor activitiesGuided toursToursLandmarks & monumentsActivities for couplesSeasonal & Holiday ActivitiesSightseeing on wheelsSightseeingNightlife & barsViewing points

Experience Chicago at night! See Buckingham Fountain's light show w/ the skyline backdrop. Ride along the lakefront to a secret spot for Navy Pier's fireworks display. An unforgettable evening awaits!

$77.70

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Chicago: History and Architecture Guided Kayak Tour

3 Reviews

ExperiencesOutdoor activitiesGuided toursWater activitiesCulture & historyOutdoor sportsToursLandmarks & monumentsSightseeingEducational activitiesWater sportsArchitecture

Paddle through downtown Chicago on a guided kayak tour of the Chicago River. Learn about the city's history, pass under ironwork bridges, and enjoy views of the skyline.

$64.31

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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: Workers Cottages of Oldtown Triangle Walking Tour

ExperiencesToursNeighborhood toursOutdoor activitiesCulture & historyLandmarks & monumentsGuided toursArtArchitectureHidden gemsEducational activitiesSightseeingPrivate tours

Embark on a captivating architecture walking tour through Chicago's Oldtown Triangle, a neighborhood rich in history and architectural charm.

$40.00

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Chicago Premium Driving Tour with River Boat Cruise

20 Reviews

ExperiencesWater activitiesFamily-friendly activitiesCulture & historyGuided toursOutdoor activitiesLandmarks & monumentsWheelchair accessibleSightseeing on wheelsToursDay tripsDay Trips FromArchitectureWater sportsViewing pointsCruises & boat toursSightseeingPrivate toursDriving experiences

See the best of Chicago in just 1 day on this guided small group sightseeing tour. Visit iconic landmarks including Architecture River Cruise, Cloud Gate "the Bean", and Adler view point.

$254.00

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Chicago: Shoreline Lake Michigan Skyline Cruise

758 Reviews

ExperiencesWater activitiesFamily-friendly activitiesToursLandmarks & monumentsOutdoor activitiesGuided toursArchitectureViewing pointsCruises & boat toursSightseeing

See the sights of Chicago from Lake Michigan on this sightseeing lake cruise. Admire stunning views of the Chicago skyline and see many of the city’s iconic landmarks.

$30.00

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Chicago: Private Catamaran Sailing for up to 12 people

ExperiencesNature & adventureToursOutdoor activitiesWater activitiesLuxury experiencesOutdoor sportsCruises & boat toursPrivate toursWater sports

This exclusive sailing experience includes breathtaking views of the Chicago skyline, refreshing swims, and the luxury of private yachting including Chicago’s largest chartered Catamaran.

$1,500.00

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City Cruises Chicago: Seadog Lakefront Speedboat Ride

642 Reviews

ExperiencesOutdoor sportsOutdoor activitiesWater activitiesGuided toursWheelchair accessibleSightseeing on wheelsNature & adventureToursCruises & boat toursViewing pointsSightseeingWater sportsExtreme sports & adrenaline

Admire Chicago’s skyline and listen to city insights during an exciting speedboat ride on Lake Michigan. Choose the extreme thrills option to enjoy even faster speeds and a chance to be splashed.

$42.78

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Chicago: Moonlight Paddle Tour on the Chicago River

11 Reviews

ExperiencesGuided toursToursOutdoor sportsWater activitiesOutdoor activitiesActivities for couplesNature & adventureSightseeingCruises & boat toursPrivate toursWater sports

Paddle along the Chicago River at night and see the city’s skyline illuminated by the moonlight. Enjoy a serene and less-trafficked route through downtown Chicago.

$57.50

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