Chicago Sailboat Rentals

Book a luxury sail & swim charter for Chicago’s Playpen today! Having hosted over 500 private charters since 2018, this 37-foot luxury sailing yacht includes world-class sailing and luxury amenities. All departures are Monroe Harbor in Downtown Chicago.

Use promo code PLAYPEN100 for $100 off any sailing adventure below!

  • Boats Provided by On A Boat Sailing Charters

    Chicago's best sailboat experience!
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