Quick Details
Sail Throughout the Season
Enjoy eligible Skyline Sails throughout the sailing season based on your selected membership level.
Skyline Sails Only
Season passes are valid for Skyline Sails only and do not apply to specialty or event sails.
Unique Membership Number
After purchase, you will receive a unique membership number to reserve eligible sails.
Priority Boarding Options
Select memberships include priority boarding before General Admission guests.
Share 10% Off
Members receive a 10% off code to share with friends and family.
ID Required
A valid ID must be shown before boarding to verify your membership.
Choose the Season Pass That Fits How You Sail
Captains Weekday Membership
Perfect for guests who want to enjoy Skyline Sails during the week.
This membership includes access to eligible Skyline Sails Monday through Friday throughout the sailing season.
Best for:
- Weekday sailors
- Flexible schedules
- Guests who want to enjoy Windy more often during the week
Captains Full Membership
A great option for weekday sailors who want an upgraded boarding experience.
This membership includes access to eligible Skyline Sails Monday through Friday throughout the sailing season, plus priority boarding before General Admission guests.
Best for:
- Weekday sailors
- Guests who prefer earlier boarding
- Members who want added convenience before their sail
Admirals Membership
A strong fit for frequent weekday guests who want priority boarding included.
This membership includes access to eligible Skyline Sails Monday through Thursday throughout the sailing season, plus priority boarding before General Admission guests.
Best for:
- Monday through Thursday sailors
- Guests who want priority boarding
- Members looking for a smoother boarding experience
Admirals Full Membership
The most flexible season pass option for guests who want to sail as often as possible.
This membership includes access to eligible Skyline Sails every day of the week throughout the sailing season, plus priority boarding before General Admission guests.
Best for:
- Frequent sailors
- Weekend availability
- Guests who want the most flexibility all season long
Membership Comparison
| Membership | Eligible Days | Priority Boarding | Best For |
| Captains Weekday Membership | Monday through Friday | No | Weekday sailing access |
| Captains Full Membership | Monday through Friday | Yes | Weekday sailing with earlier boarding |
| Admirals Membership | Monday through Thursday | Yes | Frequent weekday sailors |
| Admirals Full Membership | Every day | Yes | Maximum flexibility all season |
How Your Membership Works
1. Purchase Your Membership
Choose the season pass that works best for how often and when you want to sail.
2. Receive Your Membership Number
After purchasing your season pass, you will receive a unique membership number.
3. Reserve Eligible Skyline Sails
Use your membership number to reserve eligible Skyline Sails throughout the sailing season according to your selected membership level.
Bring Friends and Family Along
Your season pass also includes a 10% off code that can be shared with friends and family, making it easier to invite others to experience Tall Ship Windy with you.
Important Membership Details
Season passes are valid for Skyline Sails only.
Details
They cannot be used for Monday Night Blues, Fireworks Sails, Dead Theater Reckoning Co. Sails, Air & Water Shaow sails, or any other special event sails.
Memberships are limited to one membership per guest and may only be redeemed by the guest who purchased the membership. Memberships are non-refundable and non-transferable.
A valid ID must be shown prior to boarding to verify membership.
A small tax will apply due to passenger fees at Navy Pier.
Blackout dates apply, including Memorial Day Weekend, July Fourth Weekend, and Labor Day Weekend.
FAQs
What sails are included with my season pass?
Season passes are valid for eligible Skyline Sails only. Availability depends on the membership level you select.
Can I use my season pass for special event sails?
No. Season passes cannot be used for Monday Night Blues, Fireworks Sails, Dead Theater Reckoning Co. Sails, Air & Water Show sails, or any other special event sails.
Are there blackout dates?
Yes. Blackout dates include Memorial Day Weekend, July Fourth Weekend, and Labor Day Weekend.
Can someone else use my membership?
No. Memberships are non-transferable and may only be redeemed by the guest who purchased the membership.
Do I need to bring ID?
Yes. A valid ID must be shown prior to boarding to verify your membership.
Are memberships refundable?
No. Memberships are non-refundable.
Will any additional fees apply?
A small tax will apply due to passenger fees at Navy Pier.
Ready to Make Windy Part of Your Season?
Choose your Tall Ship Windy Season Pass and enjoy unforgettable views of Chicago from the water again and again throughout the sailing season.
