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  1. Chicago
  2. $99 -- Lake Michigan Summer Sailboat Cruise for 2, Reg. $259
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$99 -- Lake Michigan Summer Sailboat Cruise for 2, Reg. $259

Sold out - This deal was published May 08, 2013 and sold out May 19, 2013.
$99 -- Lake Michigan Summer Sailboat Cruise for 2, Reg. $259
By Travelzoo Staff
Cast off from Belmont Harbor and cruise Lake Michigan in a sailboat with this exclusive deal from the top-rated Chicago Sailboat Charters, featured by the Chicago Reader in a summer activities story. Subscribers have the opportunity to take a semi-private cruise this summer -- two people can spend up to 2.5 hours on the water starting at $99.

Why we love it

  • Take a semi-private cruise on Lake Michigan, regularly $259
  • Take advantage of a limited number of $99 cruises through June 16
  • Or for $129, reserve a cruise through late August
  • These semi-private cruises will set sail with up to 6 passengers aboard
  • These trips are BYOB and last up to 2.5 hours with dramatic views of the Chicago skyline
  • Earns a perfect 5-star Yelp rating
  • Upgrade to a Wednesday or Saturday fireworks cruise for an additional fee


May 8, 2013 - Aug. 31, 2013


Chicago Sailboat Charters
400 W. Belmont Harbor Drive
Chicago, IL 60657
(See Map)
Tel: 773-236-7245

What's included

  • Select:
  • For $99 (reg. $259), charter an early-season semi-private cruise for two (valid through June 16)
  • For $129 (reg. $259), reserve a semi-private cruise for two valid through Aug. 31
  • For $649 (reg. $1299), purchase a "Season Ticket" good for multiple cruises throughout the season, including unlimited "last minute" sails
  • Chicago Sailboat Charters has been sailing the waters of Lake Michigan for more than a decade. Cruises will take place with no more than six total passengers, and boats include such amenities as coolers for your drinks along with bottled water and ice (and bathrooms are available on every boat).
  • Departing from Belmont Harbor, these cruises are easily accessible from Lake Shore Drive by car or the CTA. Semi-private sails take place Monday, Tuesday and Thursday at 7 p.m., and morning weekend trips can also be reserved Saturday and Sunday at 9 a.m.

The fine print

Note: A limited number of vouchers are available for each deal. These offers may sell out before the "Time to Buy" has expired. $99 vouchers can be redeemed Saturday, May 11, through June 16. $129 vouchers can be redeemed May 11 through Aug. 31, 2013. Cruises can be booked up to 55 days in advance. Reservations are required and must be made online here. Merchant will charge fee if cancelled or rescheduled less than 10 days in advance. Not valid on July 4 or Aug. 16-18. Must be at least 12 years old to sail. Voucher is subject to fee if cancelled or rescheduled less than 10 days in advance; see merchant's website for details of fee structure. See below for full terms and conditions.

See all terms
$99   $259
62% off | 177 bought
Travelzoo deal by
Chicago Sailboat Charters
Sold out at
11:59 p.m. CT on May 19


M – F, 9am – 9pm ET

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400 W. Belmont Harbor Drive
Chicago, IL 60657
Tel: 773-236-7245

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This Travelzoo Local Deal at Chicago Sailboat Charters sold out at 11:59 p.m. CT on May 19 when 177 vouchers were purchased.

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