Welcome to Carefree Boat Club of Chicago

Experience Chicago's iconic waters your way with unlimited access to a professionally maintained fleet of premium vessels. We take care of the cleaning, maintenance, trailering and winterization, so you can enjoy the best of boating, without the hassles of ownership.

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888-447-1540

Club Form for Chicago

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Your Nearest Club Location

Chicago, IL USA

31st Street Harbor
3155 S Lake Shore Dr., Chicago, IL 60616 USA

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Chicago, IL USA

Belmont Harbor
2 W Belmont Harbor Dr., Chicago, IL 60657 USA

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Unlock Boating in Chicago

Carefree Boat Club Chicago offers three unique ways to experience the city from the water. From 31st Street Harbor near Soldier Field to Belmont Harbor in Lincoln Park, with Burnham Harbor in between, each spot provides unbeatable skyline views, easy lakefront cruising, and front-row access to all the best of Chicago summers. Whether you’re planning watersports, a fun cruise, or a relaxing outing with friends and family, Carefree makes enjoying Lake Michigan effortless and memorable.

Boating Made Easy

With low member-to-boat ratios, an easy-to-use online reservation system, and a versatile fleet ideal for fishing, cruising, watersports, or relaxing, every outing is seamless, exciting, and ready when you are. Members receive hands-on training in boat handling and docking, have unlimited access to a premium fleet, and enjoy full reciprocity at all Carefree Boat Club locations nationwide. Get in touch today and learn how you can start making memories on the water with Carefree Boat Club.

Our Fleet

Carefree Boat Club offers a diverse fleet of premium, professionally maintained vessels. Whether you're planning a relaxing cruise, a fishing trip, or a day of watersports, there's a boat for every adventure. Our fleet is regularly updated and inspected to ensure a safe, comfortable, and high-quality boating experience every time.

We make boating easy.
You make it unforgettable.

Pontoons, Center Consoles, Deck Boats, and more

Access to 147 locations across North America

Unlimited on-the-water boat training

We take care of maintenance, repairs, cleaning, & insurance

Boats are cleaned, fueled, and ready to go

What Our Members Say

“I love the variety of boats. We’re lucky to live near some of the most beautiful waters in the world, and we get to enjoy them in all these different ways. I even tried tubing, which I never thought I’d do!”

Jess, Stuart, FL

“I will never forget the smile on my grandson’s face when he caught his first bass. It’s a memory I will cherish forever. Thank you Carefree Boat Club for creating this moment for us.”

Gordon, DMV

“Every reservation feels VIP. The Carefree Team don’t just know my name, but also the names of my wife and kids. The boat’s ready when we turn up – we just jump in and go. 100% recommend.”

Paul, Tennessee

“I have boated my entire life, and nothing compares to the ease of Carefree Boat Club. No Maintenance, no slip fees, no cleaning. It’s been a game-changer for me and my family.”

Peter, New England

“Our weekends have been transformed since we joined Carefree. No more lounging around the house looking at screens. We book a boat, head down to the dock, and enjoy some great family time together.”

Nicole, California

How Carefree Boating Works
Easy as 1, 2, 3!

Step 1

Reserve Your Boat

Book your next adventure effortlessly—online or by phone. Choose your preferred boat, time, and location, and get ready for a hassle-free day on the water.

Step 2

Pick Up & Go

Arrive at the dock to find your boat waiting, fueled, and ready to launch. No prep, no stress—just step aboard and set sail.

Step 3

Enjoy

Make unforgettable memories on the water, then bring the boat back when you're done. No cleaning, no maintenance — just carefree fun. We’ll handle the rest.

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Boating Simplified. Experiences Amplified.

We believe boating should be effortless and accessible to all. Whether you’re cruising with family, casting a line with friends, or simply soaking up the serenity of the water, we want everyone to enjoy the wonders of being out on the water.

Step aboard any of our meticulously maintained vessels confident in your training and excited to make the most of the day ahead, knowing that all the boring bits of boating are being taken care of for you. Just head out, and have your best day yet!

Hours NOT spent by our members cleaning, maintaining or winterizing their boats!

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Boat Club Locations Worldwide

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With a Carefree Membership, You Get:

Affordable Boating

Enjoy all the benefits of boating for a fraction of the cost, with membership priced at approximately one-third of traditional ownership, giving you access to a premium fleet without the hassles of maintenance, docking, or insurance.

Unlimited Usage

Boat as often as you’d like - with no extra fees and no hassle. Use our online reservation system to choose the day, time, boat, and location that fit your plans. Our dock staff takes care of all the prep, cleaning, and maintenance, so your boat is ready and waiting whenever you are.

Large Variety of Boats

As a member, you get unlimited access to a diverse fleet of 18’ to 28’ powerboats -center consoles, pontoons, cruisers, deck boats, and more. Whether you're fishing, tubing, cruising with friends, or heading to your favorite dockside restaurant, we have the perfect vessel for you.

Great Availability

With our rolling reservations program, you can hold up to four bookings at a time, up to six months in advance. You’ll also have access to Spur-of-the-Moment reservations, giving you the flexibility to take out any available boat for a last-minute outing. Plus, our strict 10:1 member-to-boat ratio ensures excellent availability.

Nationwide Locations

Our members enjoy exclusive access to more than 150 locations on some of the most spectacular waterways in the world. Whether you're cruising the coast or navigating scenic rivers and lakes—at home or on vacation - Carefree Boat Club gets you on the water in the most stunning destinations.

On-the-Water Training

At Carefree Boat Club, every member begins with a NASBLA-certified boating safety course to ensure a strong foundation. From there, you’ll receive personalized, one-on-one training on the water - followed by specialty vessel instruction to prepare you for our entire fleet. Optional ongoing training is always available, so you can continue building confidence at your own pace.

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