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There is no better view of Chicago than from the water. We offer fully private experiences on Lake Michigan aboard a 2017 Cruisers 298SS South Beach Edition - a premium 29-foot sport cruiser built exactly for this. Your group of up to 6 has the entire boat. Just your crew, the skyline, and Lake Michigan. We depart from Belmont Harbor on Chicago's North Side - convenient for Lincoln Park, Lakeview, Wrigleyville, Bucktown, and Andersonville. No fighting downtown traffic, no South Side drives. Pull up, board, and you're on the water in minutes. Every charter is 3 hours and fully private. We run three time slots daily: - Morning — 10:00 AM to 1:00 PM - Afternoon — 1:30 PM to 4:30 PM (most popular) - Evening — 5:00 PM to 8:00 PM Our most popular experiences: - The Playpen: Anchor at Chicago's legendary summer boating scene. Swim, sun, socialize, watch the skyline. The quintessential Chicago lake day. - Sunset cruise: Watch the city go gold from the water as Chicago lights up for the evening. The most photogenic 3 hours in Chicago, period. - Navy Pier Fireworks: Wednesday and Saturday nights all summer — the best fireworks view in the city is not on the pier, it's from the water. Limited slots available. - Celebrations: Bachelorettes, birthdays, anniversaries, proposals, date nights, corporate outings. Private boat, your group, your music, your pace. The Boat: The 2017 Cruisers 298SS South Beach Edition is a premium 29-foot sport cruiser powered by a 380-horsepower MerCruiser 8.2L engine. Built for open water, it handles Lake Michigan conditions with confidence and covers ground quickly when you want to move. - Spacious bow seating area - perfect for sunning and photos - Aft cockpit with rear-facing lounge seating - Swim platform with ladder for easy water access - Bluetooth audio system - connect your own playlist - Cooler with ice - bring whatever you want to drink (no red wine, no glass) - USCG-required safety equipment throughout What's Included -- No Hidden Fees - Licensed USCG captain for the full charter - Fuel - we cover it, you don't - All USCG-required safety equipment - Bluetooth audio - bring your playlist - Cooler - Spacious platform You bring: Food, drinks (BYOB - alcohol welcome, 21+, no red wine & no glass), sunscreen, towels, whatever makes your time on the water yours. Add-ons: Extra hour Perfect For - Bachelorette and bachelor parties - Birthdays and milestone celebrations - Anniversary and date nights - Proposals - Corporate team outings and client entertainment - Friends and family lake days - Navy Pier fireworks from the water - Summer visitors who want the real Chicago experience About Your Captain The company is operated by a USCG-licensed captain. Your captain handles all navigation, safety, and local knowledge so you can focus on enjoying the experience. We know where to anchor at the Playpen, when to position for the best fireworks view, and how to make your 3 hours on the water feel longer than they are. How To Book Select your date and time slot and book directly. We confirm within a few hours and send everything you need to know - exact dock location at Belmont Harbor, parking details, what to bring, and contact info for your captain. The Details - Departure: Belmont Harbor, Chicago North Side - Capacity: Up to 6 passengers (private — your group only) - Duration: 3-hour minimum, additional hours available - BYOB: Yes - alcohol welcome for guests 21+ - Swimming: At captain's discretion based on conditions - Captain fee and fuel: Included in all pricing

CC
The boat was perfect. JJ is an awesome captain. Very attentive and helpful. Great vibes.
CL
JJ was an awesome host! Gave us easy to follow directions to the boat. The boat was comfortable and perfect for our afternoon in the playpen. Can’t recommend JJ enough! Can’t wait to book again!!
GC
Love jj he’s our baddie
BL
We booked a 3-hour Saturday charter with JJ for a group of 5, and it was fantastic from start to finish. JJ was an excellent communicator, giving clear instructions the whole time so we could have the best experience. He was personable and fun all while keeping us on schedule and safe. The boat itself was in great shape - newer and clearly well maintained. Overall we had a great time and would absolutely book another charter with JJ. Highly recommend!
TF
JJ was was great from start to finish. He communicated with us consistently and shared all the details. He made our experience one my entire family will remember. Looking forward to our next boat trip with JJ

You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Departure Location
Free cancellation up to 3 days before your trip.
Full refund if cancelled more than 72 hours before departure. Inside 72 hours, payment is non-refundable. No-shows forfeit the full booking. If the captain cancels due to unsafe weather or conditions, you receive a full refund or same-season reschedule. Maximum 6 passengers - no exceptions. BYOB welcome for guests 21+, no red wine or glassware aboard - cans and plastic only. No illegal substances aboard. All passengers must sign a waiver before boarding. Swimming at captain's discretion based on conditions. Captain has final authority on all safety and operational decisions at all times. Soft soles only on deck - no black-soled shoes. Cancellation & Weather We take weather seriously on Lake Michigan. If conditions are not safe, we reschedule you at no penalty - always. Our standard cancellation policy: full refund if cancelled more than 72 hours before your charter. The captain has final authority on departure decisions and your safety is always the priority.