26' Speed Boat for Chicago Cruising & Playpen

(2 bookings)
26 ft
Boat length
Up to 7
This boat is rented with a captain
Owner’s response rate

The boat

Let's get your family and friends out on the water in Chicago this summer!

The layout and size of this boat makes it perfect for Chicago coastal cruising and anchoring in the Playpen. If the Playpen is not your scene then we'd suggest taking in the incredible scenery cruising along the Chicago River and Navy Pier. Note that 4 hour bookings are not enough time to do both the River and the Playpen.

** Paddle-board, wakeboard, waterskis and/or tube are available upon request. Additional charge may be required.

THIS IS A BARE BOAT RENTAL - HIRED CAPTAIN IS REQUIRED (NOT INCLUDED IN THE QUOTED PRICING). Budget $75/hour for a captain. You will hire/pay them directly. We can connect you to a couple of our favorite and friendliest captains. We guarantee they'll make your experience unforgettable and will even get you drone photos!

What To Expect Onboard:

The 26' foot cuddy cruiser is unique in its size and seating area in the cockpit. Most cruisers have seating that breaks the boat up into different areas, but this cockpit is one big social zone with plenty of seating and large lounge areas on the front and back. We also have cushioned lounge chairs to sit/lay on the bow of the boat.

This vessel is NOT equipped with a bathroom so be prepared to dip your bottom half in the water off the back ladder. Or jump in because you're on a boat! We have a new sound system you can plug into via aux cable or Bluetooth. I cooler can be provided. Guests are encouraged to bring snacks and beverages.


We will be meeting either at Burnham Harbor or 31st Harbor. There is paid parking available. Pickup and drop-off at other Chicago harbors can be arranged for an additional fee of ~$50-75.

Rates are for boat rental only. The captain's fee is a separate transaction between renter and the captain (per Coast Guard regulations) so you will hire the captain and pay them directly. It's your day and the captain is there to make sure you fully enjoy it. You are welcome to hire your own licensed captain with owner approval. Captains typically charge $75 per hour.

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(1 rating)


Stereo Aux Input
Bluetooth audio
Floating mat
Inflatable toys
Cooler / Ice chest
Swim ladder
Children's life jackets
Snorkeling gear
Deck shower
Depth finder
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26 ft.
Rinker Boats
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/ (excl. fees)
Start time
You won't be charged yet

Ratings & reviews

(0 rating)

Boat location

Exact location information is provided after a booking is confirmed.

Your crew

Boat owner
(1 booking)
I am a Chicago native and boating enthusiast. I live in South Loop so can make it any harbor with relatively little notice (unless my fiancé and I are playing beach volleyball)! I've been operating boats my whole life and recently (May 2021) fulfilled my lifelong dream of sailing across the Atlantic! 31 days at sea from Nassau, Bahamas to Almeria, Spain (wouldn't recommend it ha). I've completed two Mack races (i.e., Chicago Yacht Club Race to Mackinac) in Cruising 2 division. I've sailed or boated to just about every coastal town in Michigan so if you're looking to do a lake crossing I'm definitely your guy. I'm super personable and fully appreciate that my role as a captain is to make sure the experience is worth every dollar you're paying. Safety first, but then fun and shenanigans. Happy to be your bartender, photographer and sunscreen supplier. I always have my drone with me so chance are you'll walk away with incredible footage for your social media.
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  • Response rate: 86%
  • Avg. response time: < 24 hours

Things to know

Allowed on boat

kids under 12
glass bottles
red wine

  • Free cancellations until 24 hours before the booking start time.
  • Cancellations within 24 hours of the booking start time are non-refundable.
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A security deposit hold (not a charge) will be placed on your credit card 48 hours before your booking starts to cover any incidental damage that may occur during your rental. This hold is released 48 hours after the booking is complete, if no claims are made. The security deposit amount for the boat you are booking will be outlined during the check-out process.

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