Chicago Playpen Sailing Charter
Sail Chicago's Playpen with a licensed captain and time to swim
From$1,219incl. taxes and fees
Duration
4 hrs
Ideal For
Up to 10 people
Includes
Sailboat, captain, safety gear
Highlights
Explore Chicago from a private sailboat charter built for swimming, photos, and time on the water. Your licensed captain selects the route based on wind, weather, visibility, and lake conditions.
- Enjoy a real sailing experience rather than only a motor cruise
- Bring your own canned drinks and snacks; glass is not allowed
- Pack layers for cooler lake weather
- Bring towels and sunscreen for swimming
What's Included
- Private sailboat charter
- Licensed captain
- Life jackets and safety gear
- Onboard bathroom
- Fuel and docking fees
Cancellation Policy
If conditions are unsafe, your charter can be rescheduled for another available date. Cancel 30+ days before: deposit non-refundable; 15–29 days: 50% non-refundable; 14 days or fewer: 100% non-refundable.
FAQs
You'll receive a detailed confirmation email with your Chicago Playpen charter details, arrival instructions, and next steps.
Captain gratuity is appreciated but not required.
Meeting details
Montrose Harbor
Experience provided by Two Brothers Sailing Chicago
Experience provided by Two Brothers Sailing Chicago
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