Skip to primary navigation Skip to content Skip to footer

Skyline Sails Membership

Unlimited Skyline Sails for Weekday or Weekends

Quick Details

  • Availability: May 1 - Sept 30
  • Duration: 75 min daily Skyline Sails!

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
$149
Weekday & Weekend Skyline Sails Membership Unlimited skyline sail cruises, limited blackout dates
$199
VIP Weekday Skyline Sails Membership Includes ticket, captain's preferred boarding
$199
VIP Weekday & Weekend Skyline Sails Membership Includes ticket, captain's preferred boarding, limited blackout dates
$249

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

Related Sails

  • Most Popular!
From $29 per Person
  • 75 minutes

Chicago Skyline Sail Aboard 148' Tall Ship Windy

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.

Anchor Book Now
Learn More