Page 3 - Outdoor activities in Chicago

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Chicago's Modern Skyscrapers Guided Walking Tour

ExperiencesLandmarks & monumentsNeighborhood toursToursCulture & historyArtWheelchair accessibleGuided toursOutdoor activitiesSightseeingViewing pointsPhotography toursArchitecture

Chicago is recognized as a leader in Modern architecture, a style that revolutionized the visual world during the mid-20th century. Learn how Chicago developed the skeleton frame Modern skyscraper and gain insights into iconic Modernist Chicago buildings.

$35.00

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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: Skyline Drone Experience with Hands-On Flying

ExperiencesOutdoor activitiesToursOutdoor sportsEducational activitiesPhotography toursWorkshops & classesSightseeingViewing pointsExtreme sports & adrenaline

Fly a drone and capture stunning shots of Chicago’s skyline on this experience. Learn the basics of drone flying from FAA certified drone pilot, watch a demonstration flight, get hands-on practice.

$189.00

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Chicago: Bikes, Bites, and Brews Biking Tour

141 Reviews

ExperiencesSightseeing on wheelsNeighborhood toursOutdoor sportsToursOutdoor activitiesGuided toursHidden gemsBeer bikesFood & drinksBike tours

Sample Chicago’s four favorite food groups – pizza, hot dogs, brownies, and beer – on this city bike tour. Tour Chicago's famous neighborhoods and top attractions, day and night tour routes.

$89.99

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Chicago: Offbeat Guided Street Art Tour

37 Reviews

ExperiencesNeighborhood toursArtCulture & historyToursOutdoor activitiesGuided toursGraffiti & urban artSightseeingEducational activities

Celebrate Chicago's vibrant street art scene on a guided walking tour of the city's most eclectic neighborhoods. Learn about the artists, their art, and the future of street art in Chicago.

$40.00

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Chicago: Lakefront, Parks, and Museums E-Bike Tour

2 Reviews

ExperiencesSightseeing on wheelsToursNature & adventureNeighborhood toursDay Trips FromGuided toursScooters & motorcyclesOutdoor sportsFamily-friendly activitiesOutdoor activitiesDay tripsPhotography toursEducational activitiesSightseeingGarden & park toursBike tours

Explore Chicago’s lakefront, parks, and museums on an e-bike tour. Glide along Grant Park’s floral paths, capture photos at Buckingham Fountain, and enjoy city views from Museum Campus.

$72.15

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Chicago: Full-Day or Half-Day Bike Rental

22 Reviews

ExperiencesOutdoor activitiesOutdoor sports

Choose between a full-day or half-day bike rental and explore Chicago at your own pace.

$23.99

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Chicago: Westside Food Tasting Bike Tour with Guide

16 Reviews

ExperiencesOutdoor activitiesNeighborhood toursDay tripsToursGuided toursSightseeing on wheelsDay Trips FromBike toursFood & drinks

Eat around the world without leaving Chicago! Enjoy the city's best ethnic cuisines while biking through its most historic neighborhoods and along the gorgeous 606 and Lakefront trails.

$99.99

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Walkin' with Colin: Chicago Tour du Jour

2 Reviews

ExperiencesNeighborhood toursCulture & historyOutdoor activitiesGuided toursToursWheelchair accessibleSightseeingHidden gems

Walkin'W/Colin is a one of a kind feet on the street experience recommended by 100% of travelers on Trip Advisor! Chicago History-Mystery-Comedy-Tragedy on a tour du jour in the heart of the city!

$44.00

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Milwaukee: Helicopter Rides Over Downtown & Lakefront

2 Reviews

ExperiencesActivities for couplesLuxury experiencesOutdoor activitiesToursNature & adventureSightseeingViewing pointsAir & helicopter toursExtreme sports & adrenaline

Soar above Milwaukee’s skyline, river, and lakefront on a thrilling helicopter ride. Choose from three unique routes for unforgettable city views.

$55.00

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Chicago Highlights Walking Tour with Skydeck & Cruise

8 Reviews

ExperiencesOutdoor activitiesCulture & historyDay tripsToursGuided toursWheelchair accessibleDay Trips FromLandmarks & monumentsWater activitiesDeals & DiscountsNeighborhood toursFamily-friendly activitiesWater sportsSightseeingPrivate toursCruises & boat tours

Explore the highlights of Chicago on a guided tour that includes a stroll around town as well as a boat cruise on the Chicago River.

$170.10

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