Sailboat Cruise for Two, Four, or Six from Chicago Sailing Charters (Up to 50% Off)

31st Street Harbor, Dock K, Slip 14

Value Discount You Save
$100 41% $41
Give as a Gift
Limited quantity available
Over 520 bought

In a Nutshell

Sit back and relax with the captain on a semi-private or private sailboat charter that floats around Lake Michigan

The Fine Print

Promotional value expires Oct 18, 2016. Amount paid never expires. Subject to weather. Advance online scheduling is required. Merchant's standard cancellation policy applies (any fees not to exceed Groupon price). Limit 1 per person, may buy 3 additional as gifts. Valid only for option purchased. Each boat can hold up to 6 guests total. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Choose from Three Options

  • $59 for a sailboat charter for two ($100 value)
  • $99 for a sailboat charter for four ($200 value)
  • $149 for a private sailboat charter for up to six ($275 value)

When booking, choose one of the following three-hour trips:

Please arrive 15 minutes before your scheduled departure time. Cruises are BYOB, as food and beverages (alcoholic and non-alcoholic) are welcome on the sailboat.

A Chat with Chicago Sailing Charters

What services does your business offer and what makes your business stand out from the competition? You are able to sit back and relax while our captain and first mate make sure you are very comfortable during your voyage. Bring your own food and beverages as well.

What is the experience customers can expect? Relaxing night under the fireworks with friends and family.

What was the inspiration to start or run this business? To get local Chicagoans and tourist out on Lake Michigan that cannot normally enjoy their time on the water.

What do you love most about your job? Being out on the water daily and seeing everyone's smiling faces as they come back into port.

Customer Reviews

Scheduling was a bit difficult but it was worth it!
Jenna E. · September 19, 2016
Exceptional experience! Our captain was great and had a great sense of humor. It was a very easy process of booking and we were able to bring our own drinks and food which worked out really well. It was a perfect mix of fun and relaxation. I'd highly recommend Chicago sailing!
Sami W. · September 18, 2016
Captain Bruce and first mate were delightful and it was a great sail. Fun, informative, and a great night!!
Dennis R. · August 15, 2016
Merchant Location Map
  1. 1

    31st Street Harbor, Dock K, Slip 14

    3155 S. Lake Shore Dr.

    Chicago, IL 60616

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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.
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