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Book tours and experiences in Chicago

Go beyond the video

Book tours and experiences in Chicago

Browse activities from local guides

ViatorFind on Viator

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

  • Boat Tour, Historic Experience, Outdoor Leisure, and Urban Adventure

  • 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.Book a stay →

  • Combine your sailing adventure with visits to Navy Pier, Millennium Park, or an architecture river cruise for a full urban experience.Book a tour →