Explore Chicago’s scenic shores with a relaxing sail around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Select from Pirates and Maritime Stories at 1pm, Architectural and Skyline Tour at 3pm and 5pm, and Sunset and Skyline Tour at 7pm.
Skyline Sails Membership
Unlimited Skyline Sails for Weekday or Weekends
Weekday Membership: Monday – Thursday
Weekend and Weekday Membership: Monday – Sunday
- Weekday Skyline Sails Membership Unlimited Monday-Friday Skyline Sails and 50% off for Saturday & Sunday Sails
- Weekday & Weekend Skyline Sails Membership Unlimited skyline sail cruises, limited blackout dates
- VIP Weekday Skyline Sails Membership Includes ticket, captain's preferred boarding
- VIP Weekday & Weekend Skyline Sails Membership Includes ticket, captain's preferred boarding, limited blackout dates
Join the family!
Enjoy the beautiful Chicago lakefront and skyline from your favorite tall ship – now with UNLIMITED ACCESS!
- Non Refundable and Non transferable, must show ID at gate to verify membership
- Friends and Family sail with you at 20% off!
- Blackout Dates: Labor Day Weekend, Memorial Day Weekend, and July Fourth Weekend
(Saturday, Sunday, Monday)
- Limit to 1 per customer, only valid for person who purchases this membership.
- Valid for Skyline Sails only, not redeemable on Fireworks or Special Event Sails