What this place feels like
Somewhat functional with somewhat trendy, somewhat enriching, somewhat iconic character.
Experience an enchanting day aboard the Tall Ship Windy, a beautifully maintained classic sailing vessel docked along East Grand Avenue in Chicago. Feel the gentle sway of the boat as warm sunlight filters through the sail canopy, with the soft creak of ropes and metal stairs underfoot inviting you to explore. The urban skyline peeks through lush green trees, combining maritime adventure with city charm. This authentic sailing experience offers travel lovers serene moments and nostalgic vibes perfectly blending history and modern urban life on the shimmering waters of Lake Michigan. Step aboard and let your spirit set sail into adventure, evocative memories, and peaceful escape right in the heart of Chicago.
Late spring through early fall for pleasant weather and calm waters
Book Viator ToursMost videos filmed Aug during summer. August is busy - one of the most popular times to visit.
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Frequently asked questions
Late spring through early fall for pleasant weather and calm waters
1–2 hours
Camera or Smartphone, Comfortable Shoes with Grip, Hat and Sunglasses, Light Jacket for Wind, and Sunscreen
Adventure Seekers, Couples, Families, Photographers, and Solo Travelers
The nearest airport is Chicago O’Hare International Airport (ORD), approximately 30 minutes by car from the downtown waterfront.
Stay in luxury hotels, boutique inns, or cozy bed and breakfasts near Chicago’s downtown lakefront for easy access to the Tall Ship Windy.
Combine your sailing adventure with visits to Navy Pier, Millennium Park, or an architecture river cruise for a full urban experience.
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One of 420 clips our travelers have filmed in Chicago