Private Sailing Charters in Chicago
Since 2015, The Salty Dog Sailing Co. has been providing authentic private sailing events on Lake Michigan with attention to detail, genuine hospitality, and a real sailing experience under the iconic Chicago skyline.
Whether you’re new to town, a longtime local, or just enjoying a short visit to Chicago, we welcome you aboard our luxurious 33-foot Dufour performance sailing yacht “Peony”, to experience the serenity, excitement, and joy of a private sail on Lake Michigan.
Affordably priced with free harbor parking and featuring morning, sunset, moonlit, fireworks, or special event cruises, we are open 7 days per week and invite you to start planning your sailing adventure today!
Let’s go sailing Chicago!
Check our our Reviews!
2026 Rates
Group 1-2
2 Hour Charter w/Paid Captain
Just for Fun with a Friend
Great for a Date / Proposal
Free Harbor Parking
Group 3-4
2 Hour Charter w/Paid Captain
Best Value for Group Size
Perfect Size for Summer Fun
Free Harbor Parking
Group 5-6
2 Hour Charter w/Paid Captain
Spread Out and Enjoy
Big Family / Party Size
Free Harbor Parking
Our Vessel
"PEONY" Dufour 325
Known for fine lines, ease-of-sail, and polished interiors, the premium Dufour brand is synonymous with luxury and high-quality craftsmanship, delivering exceptional comfort, safety and performance.


