🚤 Chicago Summer 2026 Boat Charters (Starting May)
Ready to turn your Chicago summer plans into an unforgettable day on the water? Cruise in style aboard our luxury 30-ft 2024 Chaparral 307 SSX — perfect for soaking up the sun, skyline views, fireworks, and Playpen vibes.
🎉 Great for:
-Bachelor/bachelorette parties • Birthdays • Corporate outings • Just-because days
👥 Capacity:
-Up to 10 guests + captain/crew
👨✈️ Captain Info
-Choose from our pre-approved captain list after booking
-Captains are experienced and familiar with the boat
-Booking & communication handled through boat setter
📍 Location
31st Street Harbor
3155 S. Lake Shore Dr, Chicago
🚗 Paid parking nearby | 🚕 Lyft/Uber recommended
31st Chicago Harbor
3155 S. Lake Shore Dr.
Chicago, IL 60616
🚗 Parking:
There is open pay-for-parking in close proximity to the harbor as well as street parking. Please check for any closures of the pay-for-parking.
Recommended to take Lyft/Uber to the harbor
Where You’ll Go
🏝 Chicago Playpen – Anchor, swim and relax
🌆 Skyline Cruises – Day or night
🌉 Chicago River (4-hour minimum)
🎆 Fireworks Cruises on Wednesdays @ 9PM & Saturdays @ 10PM
Boat Amenities
🔊 Premium JL Audio sound system (bring your playlist)
❄️ Plenty of cooler space + complimentary water & ice
🚿 Swim-friendly infinity step platform
☀️ Sun lounge seating
💡 Blue neon LED lights for night cruises
🚻 Restroom onboard
🍹 BYOB & snacks welcome
🦺 Life vests + tons of storage
Charter Guidelines:
Maximum of 10 passengers plus captain/crew
Must be 21 to drink alcohol
📅 Summer 2026 Events
-June: Blvck Scene Weekend
-June: Black Yacht Weekend
-June 11–14: Windy City Boat & Yacht Show
-July: 4th of July Fireworks 🎆
-July: Chicago Scene Party
-August: Chicago Air & Water Show ✈️
-August: Chicago International Boat Show
-Late Aug–Sept: Labor Day Weekend Bash