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Top 5 Best Illinois Sailing Trips

Found 4 Sailing Trips activities in Illinois. Sort by Popularity.
 

Come Sailing with us at Navy Pier: Sail Beautiful Lake Michigan

(5 of 60 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Come Sailing with us at Navy Pier: Sail Beautiful Lake Michigan Likely to Sell Out

Come Sailing with us at Navy Pier: Sail Beautiful Lake Michigan

  • Illinois
  • Superb60 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan

(5 of 24 reviews)

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. ... More

Free Cancellation
Private Tour
Start From $507.96
 
Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan Likely to Sell Out

Come Sailing with us at Navy Pier: Sunset Sail on Lake Michigan

  • Illinois
  • Superb24 reviews5

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefro....

    Free Cancellation
    Private Tour
    Start From $507.96
 
 

Chicago Skyline Sail

(5 of 24 reviews)

This is a sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air!... More

Special Offer
Free Cancellation
Private Tour
Start From $72.98
(Saving 20% ) $91.23
 
-20% Chicago Skyline Sail Likely to Sell Out

Chicago Skyline Sail

  • Illinois
  • Superb24 reviews5

This is a sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and th....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $72.98
    (Saving 20% ) $91.23
 
 

Come Sailing with us at Navy Pier - Saturday Fireworks Sail

(5 of 7 reviews)

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyli... More

Free Cancellation
Private Tour
Start From $566.82
 
Come Sailing with us at Navy Pier - Saturday Fireworks Sail Likely to Sell Out

Come Sailing with us at Navy Pier - Saturday Fireworks Sail

  • Illinois
  • Superb7 reviews5

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Na....

    Free Cancellation
    Private Tour
    Start From $566.82
 
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