See Chicago’s skyline from Lake Michigan on an evening sail
75 mins
20+ people
Lake Michigan sail, skyline views
Explore Chicago’s shores from the water and take in views of the city skyline. Choose an evening sailing time that suits your group.
All sales are final. No-shows are not eligible for rescheduling or refunds. Sails operate rain or shine; the captain may postpone departure up to 15 minutes for passing inclement weather.
Product ID: YHDDKK
Sails depart daily at 7pm. Beginning September 3, choose a 5pm Sunset Skyline Sail or a 7pm Late Summer Twilight Sail.
Trip protection lets you cancel up to 24 hours before your scheduled sail for a refund minus the trip protection and associated fees. It also applies if Tall Ship Windy cancels your sail, including because of weather. It is not necessary for VIP tickets.
600 East Grand Avenue, Chicago, IL 60611
Fun friendly staff!. Had a great sail. Family owned. Good time.
jeremiah quinn
August 30, 2026
Fun friendly staff!. Had a great sail. Family owned. Good time.
jeremiah quinn
August 30, 2026
Paddle the Chicago River past the Wild Mile and downtown skyline
Cruise Chicago by private 47 ft yacht with space for up to 12 guests
Meet Farm Animals and Native Wildlife Across Five Acres
Paddle the Chicago River and learn downtown architecture in 3 hours
Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests
Taste international dough-based treats while exploring Wynwood’s art district