Update on COVID-19:
Coronavirus Travel Restrictions, Advice and Tips.

View All Chicago Tours & Tickets

Filter


Category


Sort By


Price



Customer Rating


Time of Day


Duration

Top Chicago Sailing Trips

Loading...

4th of July Independence Celebration Aboard Chicago's Official Tall Ship Windy!

clock 2 hours
  • Treat yourself to one of the most spectacular sails of the year aboard Tall Ship Windy. The July 4th celebration in Chicago is one of the best in the nation. From spectacular music in Grant Park the entire weekend, Navy Pier fireworks on July 2nd and the celebration everywhere on July 4th – Chicago is the place to be.

    This VIP event...Read more

Chicago's Sail Grand Prix June 18-19 at Navy Pier. VIP Event Limited Tickets

clock 2 hours 30 minutes
  • On June 18 and 19 2022 ten national teams will race cutting-edge, foiling F50 catamarans – capable of speeds in excess of 100 kph – along the shores of Lake Michigan in front of the Chicago skyline.

    Mark you calendars this Father’s Day weekend for two-days of speed, drama, and thrills as the entire city kicks off Summer 2022 at Navy...Read more

Chicago Skyline Sunset Sail Aboard Official Flagship of Chicago 148' S/V Windy

clock 1 hour 15 minutes
  • The famous Tall Ship Windy sunset sail is truly famous. Used in many world-reknown photos, backdrops for special events, weddings, or just an evening out, the sunset sail aboard one of the only four-mast Schooners still in operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn...Read more

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

clock 1 hour 15 minutes
  • 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. Windy is the Official Ship for the City of Chicago. At 148 feet long, she is one of only a few 4 masted Schooners built in the United States....Read more

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

clock 2 hours
  • 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.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect...Read more

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

clock 2 hours
  • 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.  Make the experience your own.  The flexibility of a private charter allows customization of virtually any aspect...Read more

Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

clock 2 hours
  • 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. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the...Read more

Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

clock 2 hours
  • Enjoy a private two and a half hour sailing experience for up to four 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. Make the experience your own. The flexibility of a private charter allows customization of virtually any...Read more
Loading...