Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

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
  • Looks Good

    This date is 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
Was this useful?
AI Overview

Owner's Description

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

JJ

JJ

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

Reviews

5.0 (5 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.
  2. Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.
  3. Sleek 29ft Sport Cruiser | Skyline, Sunset & Playpen | Captain & Fuel Incl.
3 photos have been added by reviewers who booked this listing.
  1. CC

    Claire

    The boat was perfect. JJ is an awesome captain. Very attentive and helpful. Great vibes.

  2. CL

    Crystal

    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!!

  3. GC

    Gabrielle

    Love jj he’s our baddie

  4. 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!

  5. 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

6 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.

Similar Listings

20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!
Powerboats in Chicago · 20 guests

20 Passenger Captained Boat - $400 off Fridays and Sunday Fundays!

5.0
Superowner
Best of 2026
$700/hour
Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago
Powerboats in Chicago · 6 guests

Beautiful Four Winns 225 Sundowner Boat With Big Sound System In Chicago

4.8
$225/hour
24 Guests Captained Party & Event Boat in Chicago with Bathroom & Aqua mat
Powerboats in Chicago · 24 guests

24 Guests Captained Party & Event Boat in Chicago with Bathroom & Aqua mat

5.0
Superowner
Best of 2026
$800/hour
Navy Pier | Captain & Fuel Included | Carver Mariner 350 | Private Yacht Charter
Events in Chicago · 6 guests

Navy Pier | Captain & Fuel Included | Carver Mariner 350 | Private Yacht Charter

5.0
$275+/hour
Cruisers Y3375 Express Yacht Downtown Chicago Experience
Powerboats in Chicago · 10 guests

Cruisers Y3375 Express Yacht Downtown Chicago Experience

5.0
Superowner
$250/hour

Top Destinations Nearby

  • Limited availabilitySome departure times on this date are still available.
With Captain
  • Hourly Only
  • With Captain Only