EXPLORE LAKE MICHIGAN IN STYLE & COMFORT
Chicago Sailboat Charters
37' luxury sailboat
Up to 7 guests
Money Back Guarantee
Since 2018, On A Boat Sailing has provided private groups in the Chicago area with VIP access to the unforgettable experience of sailing, swimming, and floating on our famous Lakefront.
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Our bookings are perfect for summer birthdays, reunions, bach parties, engagements, photoshoots, and summer days with the ones you love most.
500+ 5-star reviews
Choose from our best-selling charters & cruises:
“I rented [Dragonfly] to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner. The boat is very spacious!
Dyna, Chicago, IL
Golden Sail Money-Back Guarantee
Bad weather? Unexpected issues? We recognize things come up. Our money-back guarantee ensures you have the freedom to make adjustments with ease, providing peace of mind in the weeks and days leading up to your planned outing with us.
100% Refund up to Two Weeks From Departure
50% Refund up to 48 Hours From Departure
Full Refund for Weather Related Cancellations
Swap Dates With No Fees
Subject to Availability
