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Top 10 Best Chicago Sailing Trips

Found 6 Sailing Trips activities in Chicago. Sort by Popularity.
 

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

(5 of 27 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
 
Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

  • Chicago
  • Superb27 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
 
 

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

(5 of 70 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
 
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago Likely to Sell Out

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

  • Chicago
  • Superb70 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's Fireworks Show aboard Tall Ship Windy!

(4.8 of 14 reviews)

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More

Free Cancellation
Private Tour
Start From $113.73
 
Chicago's Fireworks Show aboard Tall Ship Windy! Likely to Sell Out

Chicago's Fireworks Show aboard Tall Ship Windy!

  • Chicago
  • Superb14 reviews4.8

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....

    Free Cancellation
    Private Tour
    Start From $113.73
 
 

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

(4.8 of 20 reviews)

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This is a relaxing sailing Adventure, that you will enjoy, on Lake Michigan, while enjoying the views, and the fresh air! Fun for all ... More

Free Cancellation
Private Tour
Start From $91.23
 
Sail on Tall Ship Windy, join us for our Likely to Sell Out

Sail on Tall Ship Windy, join us for our "Chicago Skyline Sail"

  • Chicago
  • Superb20 reviews4.8

Join us for an unforgettable sail on Tall Ship Windy, Chicago's Official Tall Ship Ambassador! This ....

    Free Cancellation
    Private Tour
    Start From $91.23
 
 

Chicago Air and Water Show VIP Cruise or Skydeck Experience

(5 of 2 reviews)

Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chicago’s Air & Water Show from the Best Seat on the Lake! 10AM SAIL: Our first sail will depart at 10am sharp. Our first event wil... More

Free Cancellation
Private Tour
Start From $154.00
 
Chicago Air and Water Show VIP Cruise or Skydeck Experience Likely to Sell Out

Chicago Air and Water Show VIP Cruise or Skydeck Experience

  • Chicago
  • Superb2 reviews5

Chicago Air and Water Show 2025 Great for friends & family! PLEASE READ CAREFULLY Experience Chic....

    Free Cancellation
    Private Tour
    Start From $154.00
 
 

Monday Night Concert Series: Blues and Views Aboard Tall Ship

(5 of 2 reviews)

Book early, as these tend to sellout! you are free to move about the ship, while the music plays, everywhere.... More

Free Cancellation
Private Tour
Start From $80.72
 
Monday Night Concert Series: Blues and Views Aboard Tall Ship Likely to Sell Out

Monday Night Concert Series: Blues and Views Aboard Tall Ship

  • Chicago
  • Superb2 reviews5

Book early, as these tend to sellout! you are free to move about the ship, while the music plays, ev....

    Free Cancellation
    Private Tour
    Start From $80.72
 
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