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 on Lake Michigan
📍 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
Check out the On A Boat experience in this highlight reel:
1,000+ PRIVATE SAILING CHARTERS SINCE 2018
Trusted superhost to hundreds of guests, each & every year.
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 damage/cleaning deposit
❌ NO refueling costs
❌ NO docking fees
