NOW BOOKING SUMMER 2026
Chicago Sailing Charters & Cruises
37' luxury sailboat
Up to 7 or 12 Guests
Privately book our 37' luxury sailing yacht for an unforgettable day with your crew!
📍 Navy Pier Marina
Our Chicago sailing charters & cruises are perfect for summer birthdays, bach parties, romantic proposals, anniversaries, and more. Take in the sights, sounds, and breathtaking scenery of the Lakefront during summer.
USCG-Captain
800+ PRIVATE SAILING CHARTERS SINCE 2018
Trusted superhost to thousands of guests, each & every year.
Our Guests Love Sailing With Us
CHICAGO SAILING EXPERIENCES starting at $799
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
Three easy steps to pre-book your private boat party this summer:
STEP 1 - Choose Your Adventure
Browse our all charters & cruises page. We offer something for everyone!
STEP 2 - Recruit Your Crew
Fire up those group chats and start recruiting. Summer weekends will sell out.
STEP 3 - Lock-In Your Big Day
Book with a 50% fully-refundable deposit. Remaining balance to be auto-debited 5 days ahead of reservation.
