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Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.

Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.

With Captain

100% refund within 3 days of your trip
  • Limited availability

    Some departure times on this date are still available.

Modern sport cruiser designed for open-air lounging and smooth rides, well suited to sightseeing, unwinding, and enjoying the city from the lake.
Trips include a dedicated captain, so your group can relax and focus on the views and company instead of navigation or handling the boat.
Renters say this listing is great for:
SightseeingSunset CruisingCouplesRelaxation
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AI Overview

Owner's Description

There is no better view of Chicago than from the water. We offer fully private charters on Lake Michigan aboard a 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 the lake. We depart from Belmont Harbor on Chicago's North Side - easy from Lincoln Park, Lakeview, Wrigleyville, Bucktown, and Andersonville. No downtown traffic. Pull up, board, and you're on the water in minutes. Time Slots Charters start at 3 hours, and plenty of groups go longer. 4, 5, and 6-hour charters are some of our best days on the water. Our standard 3-hour slots: - 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 Want more time? Just ask. We'll build the schedule around your group, subject to availability. Fireworks cruises run Wednesday and Saturday nights on their own evening schedule. 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. The most photogenic 3 hours in Chicago, period. - Navy Pier Fireworks: Wednesday and Saturday nights all summer. The best fireworks view in the city isn't on the pier, it's from the water. Limited slots. - Celebrations: Bachelorettes, birthdays, anniversaries, proposals, date nights. The Boat The Cruisers 298SS South Beach Edition is a premium 29-foot sport cruiser powered by a 380-horsepower MerCruiser 8.2L. Built for open water, it handles Lake Michigan with confidence and covers ground fast when you want to move. - Spacious bow seating - perfect for sunning and photos - Aft cockpit with rear-facing lounge seating - Swim platform with ladder for easy water access - Bluetooth audio - Yeti Cooler with ice - Full USCG safety equipment throughout What's Included - No Hidden Fees Licensed USCG captain, fuel, all safety equipment, Bluetooth audio, and a cooler with ice. That's the price you see. You Bring Food and drinks (BYOB, alcohol welcome for 21+, no red wine and no glass), sunscreen, towels, and whatever else makes the day yours. Perfect For Friends and family lake days · Bachelorette and bachelor parties · Birthdays and milestone celebrations · Anniversaries and date nights · Proposals · Corporate outings and client entertainment · Navy Pier fireworks from the water · Visitors who want the real Chicago Your Captain Every charter runs with a USCG-licensed captain who handles all navigation, safety, and local knowledge so you can focus on the day. We know where to anchor at the Playpen, when to position for the best fireworks view, and how to make the time on the water feel like more. How To Book Pick your date and time and send us an inquiry. Tell us how long you want to go out and what you have in mind, whether that's the Playpen, sunset, fireworks, or a celebration, and we'll send an offer back. Once you accept, we'll get you everything you need: exact dock location at Belmont Harbor, parking details, what to bring, and your captain's contact info. The Details Departure: Belmont Harbor, Chicago North Side · Capacity: up to 6 · Duration: 3 hours and up, with 4, 5, and 6-hour charters available · BYOB: yes, 21+ · Swimming: at captain's discretion based on conditions · Captain and fuel: included in all pricing

JJ

JJ

4 total bookings
Capacity
6 guests
Luxury, Events & Large groups
Passenger Boat

Reviews

5.0 (2 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. BL

    Bridget

    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!

  2. TF

    Tim

    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

JJ

JJ

4 total bookings

Features & Details

  • Cruisers Yachts
  • 298 SS
  • Capacity: 6 people max

Safety Equipment

Anchor & Rode
Bilge Pumps
Fire Extinguishers
First Aid Kit
Flares
Kill Switch Lanyard
Life Jackets (7)
Lifebuoys
Life-Saving Appliances
Medical Supplies
Navigation Lights
Navigation Equipment
PFDs (9)
Sound Signals
Tool Kit
VHF Radio

Operating Equipment

GPS ChartPlotter
Depth Sounder

Guest Amenities

Cooler
Shower
Sink
Toilets (1)
Washrooms Onboard

Leisure & Entertainment Equipment

Bluetooth
Sound System
Outdoor Sun Bed

Accessories

Water Mat

Departure Location

The boat's approximate location on a map

You’ll get helpful information for your departure after your booking is confirmed.

Street Address For Arrival

Street Address For Arrival

Belmont Harbor Boat Docks, Chicago, IL, USA
Chicago, Illinois, 60657
United States
Departure Location

Departure Location

41.946224,-87.6388732
Chicago, Illinois, 60613
United States

Cancellation Policy

Free cancellation up to 3 days before your trip.

Additional Terms & Information

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.

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Top Destinations Nearby

  • High DemandSeveral others are asking about this available date.
With Captain
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  • With Captain Only