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Chicago Sailboat Charters

Chicago Sailboat Charters 312-834-7245


  • Private Sailing

  • Value/Semi Sails

  • Power Boat Rentals
  • Reservations
    • Availability
    • Redeem a Voucher
    • Purchase Seats
  • Photos
  • Upgrades
  • FAQ/Info
    • FAQ
    • Terms
      • Private Sailing
      • Semi-Private Sailing
    • Directions
    • Reviews
    • Why Choose Us?
  • Contact Us
  • Why Choose Us?
Use a voucher 

First Class Sailing- Quick Links

Please click here for information about expired vouchers and extensions.

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Reserve a sail using your voucher(s)

Confirm your existing reservation

Availability       FAQ          Terms

2-person sailing will be discontinued as of 7/1/22. If unused by then, the amount paid for unused vouchers can be used towards a 6-person sail.

Labor Day w/e 20% OFF
20% OFF Sat/Wed FIREWORKS rides
$649 9am power boat rides
20% OFF Labor Day Weekend

See all Specials

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Chicago Sailboat Charters

400 W Belmont Harbor Dr
Chicago, Illinois 60657
Phone: (773) 236-7245

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