Quick Details
Adult Ticket
Ages 13+
$ 49
Child Ticket
1 to 12 years of age
$ 34
Infant Ticket
0 to 12 months of age
$ 10
Adult Admirals Ticket
Ages 13+ • Includes ticket, trip insurance and VIP boarding line
$ 69
Child Admirals Ticket
1 to 12 years of age • Includes ticket, trip insurance and VIP boarding line
$ 49
Group Rates
20+ Person Group
Adult Tickets
20 - 39 People • Price per person
$ 35.28
Adult Admiral Tickets
20 - 39 People • Price per person
$ 62.10
Adult Tickets
40+ People • Price per person
$ 33.32
Adult Admiral Tickets
40+ People • Price per person
$ 58.65
Infant Tickets
0 to 12 months of age - Adults must be selected first
$ 8
Experience Chicago’s Stunning Skyline from the Water!
AVAILABLE NOW SAIL DAILY May 15, THROUGH Sept 27!
Leave the hustle and bustle behind! Explore Chicago’s shoreline, with a leisurely trip on Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water. This May or may not include storytelling, look at each date and time, for those details. If nothing noted, it will include a variety of music, played at background levels, for your enjoyment while quietly sailing.
We also have refreshing beverages, and snacks from the ships store (full bar & gift shop)!
For those desiring something more exclusive, our VIP Ticket, may be just what you looking for!
To book now, click a date to browse availability and select your preferred sail time.
More info
For group tickets, for groups of 20 or more, use our “Book for Groups” button, for your group discount!
BACK AGAIN 2026 – Season memberships are available! One purchase to sail unlimited skyline sails!
Go to our memberships page for all the details!
Private Charters – Please visit our private charters page for more info or download our charters fact sheet here.
Optional Items:
These can be added to your reservation while booking
-
- Ticket
- VIP boarding, this is a separate boarding line, which boards first!
- Trip insurance – see description below
- Taxes & Fees
-
- Windy Drink Tickets: $10 value redeemable for drinks only. No cash value. Non-refundable. Only valid on the trip purchased.
- Trip Insurance: Price varies due to the cost of each ticket. You must purchase for all tickets in your reservation. Recommended, but not required. This gives you the ability to cancel your reservation and receive a full refund (less the cost of insurance).
- Examples:
- You contact us, 24 hours before your tour, we will refund you tickets (less cost of insurance
- We CANCEL or postpone your tour, we will refund you tickets (less cost of insurance
- No insurance – if we cancel or postpone, you will be offered a credit, for a reschedule of your sail.
- NO REFUNDS given without insurance.
-
- No-shows will be charged the full price. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture. We leave ON-TIME – Be Early!
- The captain reserves the right to postpone the sail for up to 120 minutes; if the sail is cancelled, tickets may be exchanged for another time. We will text , and email, everyone IF a decision is made. If, weather is challenging, pay close attention to your phone (make sure you have the phone listed on the reservation with you!!)
- All sales are final.
- No refunds and no exchanges are available without the purchase of additional Trip Insurance. The Windy sails rain or shine.
Enjoy the beautiful Chicago lakefront and skyline from your favorite tall ship throughout our sailing season with our memberships. Once you purchase your membership, you’ll be able to join us during our Skyline Sails throughout the sailing season for *no additional cost. After purchasing your membership, you’ll receive a unique membership number that can be used according to the membership level you selected, along with a code for 10% off to share with friends and family.
*Please note, a small tax will apply due to passenger fees at Navy Pier, for each use.