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  • Frequently Sells Out

Chicago Skyline Sunset Sail

Quick Details

The famous Tall Ship Windy Sunset Sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings and evenings out, the sunset sail aboard one of the only four-mast Schooners still in operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn toward the Chicago skyline for a view of our spectacular sunset. Sit back and relax, enjoy some soothing music and gently complete your day with this dramatic sunset.

Standard Boarding
Adult Ages 13+
$59
Child Ages 0-12
$49
VIP Captains Boarding
Adult Ages 13+
$69
Child Ages 0-12
$59

Chicago’s Tall Ship Windy Sunset Cruise departs Navy Pier promptly at 5pm. The sunset cruise tends to sell out so we highly recommend the purchase of VIP tickets to ensure your choice of seating.

Private Charters

Please visit our private charters page for more info or download our charters fact sheet here.