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  1. Chicago
  2. $99 -- First-Class Summer Sailboat Cruise for 2, Reg. $199
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$99 -- First-Class Summer Sailboat Cruise for 2, Reg. $199

Sold out - This deal was published March 11, 2014 and sold out August 11, 2014.
$99 -- First-Class Summer Sailboat Cruise for 2, Reg. $199
By Karl Klockars
Sailing the waters of Lake Michigan for more than a decade, Chicago Sailboat Charters earns a perfect 5 stars on Yelp for their first-class sailboat trips. 

Why we love it

  • All sailboats are at least 36- to 39-feet long and are built for comfort and speed
  • Cruises depart from a private dock at Belmont Harbor and provide fantastic skyline views
  • All trips are two-and-a-half hours and are BYOB
  • Park at the gated dock for $12 or park a short walk away for free; near public transit
  • Valid on Memorial Day and Labor Day weekends


May 16, 2014 - Sept. 14, 2014


Chicago Sailboat Charters
400 W. Belmont Harbor Drive
Chicago, IL 60657
(See Map)

What's included

  • For $99 (reg. $199), two can take a first-class semi-private sailboat cruise
  • Boats can easily fit eight to 10, but CSC limits these trips to six passengers for comfort and space
  • All boats are guaranteed to be 36-foot boats or larger, with coolers and iPod hookups (and bathrooms)
  • For $299 (reg. $597), reserve a larger 39-foot vessel for a charter; bring up to six guests
  • Trips available at sunset on Monday, Tuesday and Thursday as well as Saturday and Sunday mornings; more details here

The fine print

Valid May 16, 2014 - Sept. 14, 2014; final day to make reservations is Sept. 5. Reservations required; subject to availability and are recommended to be made at least 10 days in advance. For semi-private sails, visit this site and follow site instructions to make a reservation. For $299 Reserved cruises, call to reserve. Tax and gratuity are not included; a 9% Chicago amusement tax will be assessed at time of reservation. Please tip on the full value. All sales final; no refunds or exchanges. Once purchased, vouchers are subject to merchant's rescheduling policy; details can be found here.  Valid for two or six people. Not valid July 3-4 (evenings) or Aug. 16-17. Must be at least 12 years old to sail. Subject to weather conditions. Must sign waiver to sail. Must be of legal age to consume alcohol. 

See all terms
$99 May 16, 2014 - Sept. 14, 2014   $199
50% off | 289 bought
Travelzoo deal by
Chicago Sailboat Charters
100% Enjoyed Chicago Sailboat Charters
100% (5 ratings)
Sold out at
12:06 p.m. CT on Aug. 11


M – F, 9am – 9pm ET

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400 W. Belmont Harbor Drive
Chicago, IL 60657

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This Travelzoo Local Deal at Chicago Sailboat Charters sold out at 12:06 p.m. CT on Aug. 11 when 289 vouchers were purchased.

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