Chicago Skyline Sail
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; minimal physical activity required
Overview
Discover Chicago's stunning skyline from Lake Michigan with a private sail on Tall Ship Windy. This personalized boat tour offers breathtaking views, perfect for special celebrations or outdoor enthusiasts. Book your unforgettable adventure today!
Chicago Skyline Sail
All ages • 75 Minutes • Great for friends & family!
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About This Adventure
Experience the beauty of Chicago from the water with a 75-minute sail on Lake Michigan. Enjoy breathtaking views of the iconic skyline and unwind as you watch the sunset. Available daily from May through October, this unique adventure offers a perfect escape from the city's hustle and bustle.
Duration
Each sail is approximately 75 minutes.
About
AVAILABLE NOW SAIL DAILY MAY THROUGH OCTOBER 1!
Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views and discover the Windy City from the water.
- 7pm Daily: Sunset and Skyline Sail
Beginning September 3: Enjoy a Sunset Skyline Sail at 5pm and a Late Summer Twilight Sail at 7pm
To book now, click a date to browse availability and select your preferred sail time.
More info
For groups greater than 19 please use the group reservation or call!
Adventure Tips
Arrive Early for the Best Views
Arriving 15-20 minutes early ensures you get a great spot on the boat and have time to settle in before departure.
Dress for the Weather
Bring layers and windproof clothing to stay comfortable, especially if the weather is cooler or breezy on the water.
Bring Your Camera
Capture stunning skyline views and cityscapes from the deck; a waterproof case can help protect your gear from splashes.
Book in Advance
Private boat tours can fill up quickly, so reserve your preferred date early to secure your spot and customize your experience.
Local Insights
Wildlife
- Seagulls
- Bald eagles
History
The Tall Ship Windy has been a part of Chicago’s waterfront since 1976, offering classic sailing experiences and maritime history aboard a traditional schooner.
Conservation
The operation emphasizes sustainable sailing practices, reducing emissions and supporting Lake Michigan’s health through eco-friendly initiatives.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Sunglasses
Protect your eyes from the sun and glare off the water during a sunny sail.
summer|null specific
Hat or Cap
Shield your face from the sun and reduce glare for better viewing and photos.
summer specific
Windproof Layer
Keep warm on the water as it can be breezy and chilly, especially outside of summer.
spring|fall|winter specific
Waterproof Jacket
Stay dry and comfortable if splashes or rain occur during your sail.
spring|fall|winter specific