What this place feels like
Expect somewhere no-frills, adventurous and sociable.
Tall Ship Windy
Book Viator ToursEmbark on an unforgettable maritime adventure aboard the Tall Ship Windy in Chicago's iconic harbor. Feel the wind in your hair and the sun on your face as you navigate historic waters with the stunning Chicago skyline towering around you. This breathtaking sail effortlessly blends exhilarating nautical thrills with serene moments on the shimmering lake, inviting travel lovers to immerse themselves in a timeless experience filled with salty air, creaking ropes, and panoramic city views. Whether you're a sailing novice or ocean enthusiast, surrender to the call of the water and discover Chicago from a spectacular new perspective.
Late spring through early fall for ideal sailing weather and scenic views.
Most videos filmed Aug during summer. September is quiet - more local atmosphere, fewer tourists.
What this place feels like
Expect somewhere no-frills, adventurous and sociable.
Frequently asked questions
Late spring through early fall for ideal sailing weather and scenic views.
1–2 hours
Camera or smartphone for photos, Comfortable shoes with grip, Light jacket for breeze, Sunglasses and sun protection, and Water bottle
Adventure Seekers, Couples, Families, Photography Enthusiasts, and Solo Travelers
Fly into Chicago O'Hare International Airport (ORD), approximately 30 minutes from East Grand Avenue by car or public transport.
Stay near the harbor at downtown hotels, boutique stays along the Magnificent Mile, or charming guesthouses in the Lakeshore East neighborhood.
Explore nearby Navy Pier attractions, stroll the Chicago Riverwalk, or visit the Art Institute of Chicago for a cultural day out.
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One of 437 clips our travelers have filmed in Chicago
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