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First-Class Sailing for Two or Six from Chicago Sailboat Charters (Up to 50% Off)

Chicago Sailboat Charters - Chicago

91% of 23 customers recommend

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In a Nutshell

Captains ferry groups of up to six onto Lake Michigan for relaxing excursions and stunning views; patrons can bring their own beverages

The Fine Print

Promotional value expires Sep 15, 2014. Amount paid never expires. Limit 1 per person, may buy 2 additional as gifts. Limit 1 per visit. Must sail by expiration date on your Groupon. Reservation required. Must sign waiver. Not valid for July 3/4 evenings or Aug 16-17 daytime sailing. Sailing takes place Monday, Tuesday, and Thursday evenings at sunset, or Saturday and Sunday mornings. All children must be 12 or older. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.


Choose Between Two Options

  • $99 for first-class sailing for two ($199 value)
  • $299 for luxury first-class sailing for six ($597 value)

Sailing trips last for 2.5 hours, and take place on Monday, Tuesday, and Thursday evenings at sunset, or Saturday and Sunday mornings. All outings take place on 36'-39' boats, with the six-person outing guaranteed to take place on a 39' boat.

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.


91% of 23 customers recommend

  • “Be early, bring extra warm clothes and be ready for a great time on the water. Excellent Captains, Rob and Cory!”

  • “Great experience”

  • “We enjoyed a lovely cruise out on Lake Michigan.”

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    400W Belmont Harbor Drive

    Chicago, IL 60657


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Outdoor activities, from cycling to sailing
15% Bonus Savings
Get an extra 15% off local restaurants, spas, salons, and more to use within 48 hours of your Goods order! See details
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.