Semi-Private Weekday or Weekend Sailing for Two from Chicago Sailboat Charters. Two Options Available.

Chicago Sailboat Charters

Up to 52% Off
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Customer Reviews

30 Ratings

100% Verified Reviews
All reviews are from people who have redeemed deals with this merchant.
Relevant Reviews


Crystal P. · 3 reviews TOP REVIEWER
· Reviewed August 12, 2017
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!


Stuart L. · 1 reviews
· Reviewed July 9, 2017
Great activity. Captain was friendly and great sailor. Got lucky with impeccable weather. Lots of fun and would definitely do again.


Greg L. ·
Reviewed September 15, 2015
Be early, bring extra warm clothes and be ready for a great time on the water. Excellent Captains, Rob and Cory!

What You'll Get

Sailing gained popularity during the Renaissance, when painters crossed large bodies of water using only canvas sails and camelhair-tipped oars. Carry on artistic traditions with today’s Groupon from Chicago Sailboat Charters. Sailing trips depart Belmont Harbor at 7 p.m. Monday–Thursday and at 9 a.m. Saturday and Sunday. Choose from the following options:

  • For $125, you get two seats on a weekday (Monday through Thursday) 2.5-hour sail (a $260 value).
  • For $130, you get two seats on a weekend (Saturday or Sunday) 2.5-hour sail (a $260 value).

Chicago Sailboat Charter’s experienced captains guide semi-private tours on a fleet of sailboats, two of which are new additions that ensure a safe and authentic journey. During a weekday nighttime sail, you and a fellow seafarer can glide along the darkened waters while admiring the lights shining from Chicago's landmarks, neighborhoods, and diamond-encrusted pizzeria awnings. Alternately, opt for a weekend-morning sail to swap a daily caffeine injection for invigorating views of Lake Michigan's shimmering water and stray moonbounces. Each trip sends up to six passengers skimming over Mother Earth’s liquidy skin, but note that this Groupon gets you only two of those seats. Customers who sign up for the newsletter before June 15 get a $15 credit toward any upgrade and a lifetime supply of quiet satisfaction.

Although Chicago Sailboat Charters sometimes offers discounts, this Groupon still presents the best deal.

The Fine Print

Promotional value expires Sep 4, 2011. Amount paid never expires. Limit 2 per person. Limit 1 per visit. Valid only for option purchased. Must be 12 or older. Fee of at least $10 may apply for cancellations. Subject to weather. Not valid on 7/4, 8/20, or 8/21. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

About 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.

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.