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400 West Belmont Harbor Drive, Chicago

Two-Hour Luxury Sailing for Up to Two or Six from Chicago Sailboat Charters (Up to 49% Off)

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Captains ferry groups of up to six onto Lake Michigan for relaxing excursions and scenic views

Customer Reviews

100% Verified Reviews
All reviews are from people who have redeemed deals with this merchant.
11 ratings9 reviews
October 6, 2020
Amazing experience
8 ratings2 reviews
September 27, 2020
We had an awesome private sail with our group of four adults. Loved it and will book again next season. Thank you!
25 ratings13 reviews
September 3, 2020
Great experience! Matt the captain was great, and my husband and I did have a wonderful time!!
13 ratings5 reviews
August 7, 2020
Had a interesting time. Captain was incredibly knowledgeable as well as entertaining. A couple of passengers on the boat argued the entire time making the trip less enjoyable. It was like we were on a reality television show. If interested book with friends or book alone...not with random strangers.
11 ratings4 reviews1 photos
October 1, 2019
We had a great experience. Captain very informative! It was a very rough day, but had the option to rebook but ventured out anyway.
1 ratings1 reviews
September 17, 2019
We had a wonderful afternoon, fun & sun!! Exceeded our expectations!
7 ratings5 reviews
September 17, 2019
Captain was terrific, great time.
9 ratings6 reviews
August 2, 2020
Chicago Sailboat Charters is an incredible experience! Clear, easy communications, incredibly accommodating, easy to book, truly a first-class service. The freedom felt in being under the sails was worth everything. CSC will definitely be on the agenda next season!
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Customer Photos

  • Photo submitted by Linda

About This Deal

After Your Purchase
After Your Purchase
After purchasing this deal, you'll need to visit the merchant's website to complete redemption. Learn more here.
  • Must be 12 or older
  • Departure location: North End of Belmont Harbor, H Dock Gate, 400 West Belmont Harbor Drive, Chicago, IL
  • Departure times: by appointment, check availability here
  • Sailing takes place Monday, Tuesday, Thursday Nights, and Saturday and Sunday mornings.
  • Six-person option can also take place most weekdays during the daytime at 9 a.m., 12 p.m., or 3:30 p.m.
  • The vessel: 36′–39′-long six-person sailboat
  • Availability may be limited on July 3–4 and August 14–15, 2021

Need To Know

Promotional value expires Sep 15, 2021. Amount paid never expires. Must be 12 or older. Online reservation required. Not valid on July 3–4 and August 13–14, 2021. Must sign waiver. Merchant's standard cancellation policy applies (any fees not to exceed voucher price). Limit 1 per person, may buy 2 additional as gift(s). May be repurchased every 90 days. Limit 1 per visit. Valid only for option purchased. 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.