Skyline Sail

Discover the famous Windy City from the water!

Adult
$30
Child
$10

The Best Way to View Chicago’s Skyline

Enjoy a leisurely cruise as you take in the world-famous skyline of Tall Ship Windy City from the water.

Leave the hustle and bustle behind! Explore Chicago’s shores and watch the sunset with a leisurely trip around Lake Michigan.

Take in the world-famous skyline, enjoy spectacular views, and discover Tall Ship Windy City from the water… all from the decks of the famous Tall Ship Windy.

Start Time

Low Season schedule please refer to our website for dates and times
May – Skyline sails at 1:00 and 3:00 Daily – Check Website for exact times

Sails at 7:00 and 9:00 daily, exceptions by month stated below
June – Offered Daily – with the exception of Firework Sails and Special events
July – Offered Daily – with the exception of Firework Sails and Special events
August – Offered Daily – with the exception of Firework Sails and Special events
Sept – Limited Schedule – Check Website

Duration

75 minutes


Cancellation Policy:

No refunds, no exchanges without the purchase of additional trip insurance: Rain or shine event. 

No-shows will be charged the full price. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.

All sales are final. The captain reserves the right to postpone a sail for up to 120 minutes; if the sail is canceled, tickets may be exchanged for another time.

No refunds, no exchanges without the purchase of additional trip insurance. Sailing on the Windy is a Rain or shine event.

Read More

Skyline Sail

Discover the famous Windy City from the water!

Adult
$30
Child
$10

The Best Way to View Chicago’s Skyline

Enjoy a leisurely cruise as you take in the world-famous skyline of Tall Ship Windy City from the water.

Leave the hustle and bustle behind! Explore Chicago’s shores and watch the sunset with a leisurely trip around Lake Michigan.

Take in the world-famous skyline, enjoy spectacular views, and discover Tall Ship Windy City from the water… all from the decks of the famous Tall Ship Windy.

Start Time

Low Season schedule please refer to our website for dates and times
May – Skyline sails at 1:00 and 3:00 Daily – Check Website for exact times

Sails at 7:00 and 9:00 daily, exceptions by month stated below
June – Offered Daily – with the exception of Firework Sails and Special events
July – Offered Daily – with the exception of Firework Sails and Special events
August – Offered Daily – with the exception of Firework Sails and Special events
Sept – Limited Schedule – Check Website

Duration

75 minutes


Cancellation Policy:

No refunds, no exchanges without the purchase of additional trip insurance: Rain or shine event. 

No-shows will be charged the full price. Guests must arrive at least 30 minutes before the scheduled departure time or risk forfeiture.

All sales are final. The captain reserves the right to postpone a sail for up to 120 minutes; if the sail is canceled, tickets may be exchanged for another time.

No refunds, no exchanges without the purchase of additional trip insurance. Sailing on the Windy is a Rain or shine event.