Sailing Excursion for Two or Season Pass from Chicago Sailboat Charters (Up to 57% Off). Three Options Available.

North Side

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In a Nutshell

Captains ferry groups of up to six onto Lake Michigan along the shoreline or straight out for relaxing excursions and stunning views

The Fine Print

Expiration varies. Amount paid never expires. Limit 3 per person, may buy 1 additional as a gift. Limit 1 per visit. Valid only for option purchased. Online reservations required 10 days in advance. Subject to weather. Fee of $15 to $85 may apply for cancellations. Must be 12 or older. Must sign waiver. Not valid 7/4 or 8/16-18. All sails from 5/11-7/15 are 2.5 hours; all sails from 7/16-8/31 are 2 hours. Must use promotional value in 1 visit. 9% Chicago amusement tax not included. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Ancient sailors used to navigate by consulting the North Star, until it lost its way during its twenties and decided to just head west to see what happened. Enjoy modern sailing with this Groupon.

Choose from Three Options

  • $119 for a semiprivate sailing excursion for two from May 11–June 9 (a $279 value)
  • $139 for a semiprivate sailing excursion for two from May 11–August 31 (a $279 value)
  • $649 for a season pass for two from May 11–August 31 (a $1,299 value)

All sails between May 11 and July 15 are two and a half hours, while sails between July 16 and August 31 are two hours. Semiprivate sails are shared and will include up to six passengers. Semiprivate sails take place on Monday, Tuesday, and Thursday nights at 7 p.m., as well as Saturday and Sunday mornings at 9 a.m. Season passes are good between May 11 and August 31 for five semiprivate sailing excursions—two standard sails, one fireworks upgrade sail, and two weekend upgrade sails—plus as many last-minute sails as are available. See more information about upgrades here.

Chicago Sailboat Charters

The minds behind Chicago Sailboat Charters share their passion for the sailing experience by making waterborne adventuring accessible to the general public with group sailing charters. Fostering the atmosphere of a private charter, the captains ferry passengers out onto Lake Michigan for stunning views of Chicago's skyline. The crew encourages its guests to make the most of the trip by providing a bathroom, bottled water, ice for drinks, and plenty of cooler and storage space, while encouraging guests to bring their own, snacks, drinks, and an inflatable blanket for a picnic out on the lake.

Customer Reviews

Our evening was absolutely amazing! Rob was the perfect captain and made our sail enjoyable. We would definitely recommend sailing with them. We can't wait to come back and do it again!
Crystal P. · 7 days ago
Great activity. Captain was friendly and great sailor. Got lucky with impeccable weather. Lots of fun and would definitely do again.
Stuart L. · July 9, 2017
Be early, bring extra warm clothes and be ready for a great time on the water. Excellent Captains, Rob and Cory!
Greg L. · September 15, 2015

By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.