NOW BOOKING SUMMER 2025
Chicago Sailing Charters & Cruises
37' luxury sailboat
Up to 7 guests
Money Back Guarantee
On A Boat Sailing is the premier boating charter for small group celebrations in Chicago.
Our 37' luxury sailing yacht is perfect for summer birthdays, not-so-basic bach parties, romantic proposals, content creation, and more. Everything's a little bit better from Lake Michigan!
500+ 5-star reviews
PRIVATE SAILING CHARTERS & CRUISES starting at $999
Looking to Sail & Swim with more than 7 guests?
Check out Sailing Chi's Sail & Swim+ for more time on a larger boat with a bigger group of your friends!
New in 2025: all-inclusive sailing packages!
Book any Sail & Swim Playpen Charter or Navy Pier Fireworks Cruise this season, and we'll throw in our welcome package at no additional cost. That means fewer coolers to carry, less ice to lug, and more time to focus on making memories with your favorites.
Your all-inclusive booking includes:
🥂 Complimentary Champagne Toast
🍻 (Pre-chilled) 12-pack of High Noon Vodka Seltzers
🥜 Unlimited Snacks & Non-Alcoholic Drinks
Start planning with our summer 2025 calendar now:
No hidden fees. No surprise charges. 100% transparent pricing.
❌ NO hourly captain fees
❌ NO refueling costs
❌ NO docking fees
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
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 paid at end of experience.
