NOW BOOKING SUMMER 2026
On A Boat Sailing - Chicago, IL
Private Charters & Cruises
Licensed & Insured
Up To 7, 10 or 12 Guests
Concierge-level service and premium location
📍 Navy Pier Marina, Downtown Chicago
Our Chicago sailing charters & cruises are perfect for small group birthdays, wedding parties, romantic proposals, anniversaries, and more. Take in the sights, sounds and awe-inspiring scenery of the Chicago Lakefront.
USCG-Certified Captain
All bookings protected by our "Golden Sail" Money-Back Guarantee
CHICAGO SAILING EXPERIENCES starting at $135/person
1,000+ PRIVATE SAILING CHARTERS SINCE 2018
Trusted superhost to hundreds of guests, each & every year.
ABOUT ON A BOAT SAILING
What makes us different?
We provide a luxury sailboat charter that specializes in private sailing cruises for small groups. If you appreciate attention to detail, hospitality, and comfortable amenities, this is the Chicago sailing experience for you!
25 YEARS OF SAILING EXPERIENCE
Captain Greg and First Mate Cait are world-class sailors. Their resumé includes a 9-month, 6,000 nautical mile voyage from Chicago to the Bahamas and back from October 2020 to July 2021 completing "America's Great Loop". They share their passion for sailing and affinity for Lake Michigan with guests every year.
LUXURY SAILING YACHT & AMENITIES
Enjoy private access to a french-built Jeanneau Sun Odyssey, offering the flexibility of adventurous sailing with the option to drop anchor & swim on the Lake. Passenger amenities include spacious seating, Bluetooth surround-sound speakers, complimentary ice, beverages, snacks, a private bathroom with rinse shower, changing rooms, pool floats and Lilly Pad. Catering and drink packages available.
CONCIERGE-LEVEL SERVICE
This isn't like other boat rentals that provide barebones and an old salty captain. Our custom charters go above and beyond to provide luxury, comfort and style for your group. It's walk-on walk-off boating in the heart of the city. No request is too small. Want to decorate the boat for a party or proposal? We do that and more while matching the energy and vibe you are looking for on the boat!
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
No hidden fees. No surprise charges. 100% transparent pricing.
❌ NO damage/clening deposit
❌ NO refueling costs
❌ NO docking fees
