'Sailing Chicago's Gorgeous Lakefront' is a pet-friendly Airbnb Experience hosted by Dan and Jen. Sail from DuSable Harbor to favorable winds led by Captain Dan. Your host will take care of the sailing, but is happy to guide you if you want to join in. Dogs are welcome and your host has some sizes of dog life jackets. Let them know first to see if they have the right size for your pooch. The experience lasts 3 hours and can accommodate up to 10 guests ages 5 and up. Life jackets are required for non-swimmers. Rates start at $160 per person.
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