Charter Services
Every charter is operated by a USCG-licensed captain. Revenue funds maritime scholarships through Sail Shop Chicago NFP.
Scenic Cruises
From $200/hrRelax on a private cruise along the Chicago skyline and Lake Michigan. Sunset, daytime, and moonlight options available.
Dive Charters
From $400Explore Lake Michigan shipwrecks and reefs with PADI-certified dive captains. All experience levels welcome.
Corporate Events
From $800Team building, client entertainment, and celebrations on the water. Customizable packages for groups up to 50.
Fishing Charters
From $400Guided fishing trips for salmon, trout, and perch. Equipment provided. Half-day and full-day options.
Sailing Instruction
From $200Learn to sail with ASA-certified instructors. From beginner basics to advanced certification courses.
Fireworks Cruises
From $300Watch Navy Pier and lakefront fireworks from the best vantage point — on the water. Seasonal availability.
Playpen Cruises
From $300Join Chicago's floating party at the Playpen sandbar. Perfect for birthdays, bachelor/ette parties, and summer fun.