Boats for sale in Chicago Illinois

With only 98 hours on it this 21' H2O Sport has had a cushy freshwater life on Lake Michigan and has always been rack stored indoors since new. She performs like a BMW 3 Series on... View Details

The 191 Suncoast breaks down boating to its basics, while not sacrificing the Chaparral design, style, and quality you have come to expect. A large open concept seating arrangement... View Details

Meet your next on-the-water obsession: the 2016 Chaparral 307 SSX  a head turning mix of luxury, performance, and pure boating bliss! At 30 feet, she delivers a ride as smooth as s... View Details

If you are looking for a small family cruiser with all the amenities you just found it! This Chaparral Signature 300 has all the creature comforts including Air Conditioning, Fusio... View Details

Stock #457168 Reason for selling is "Bought another boat". ANY and ALL offers will be put in front of our seller! Submit your offer today! Two Berths, Slip and Storage Prepaid t... View Details

Sharp, powerful Chaparral 287 SSX. Includes Volvo Penta 6.2L, 430 HP with DTS. Just 260 engine hours. Don’t miss out on this nicely maintained Chaparral 287 SSX. This 9-foot beam... View Details

One-Owner, Fresh-Water, rack-stored Chaparral 307 SSX. Plushness and Performance! Loaded with all of Chaparral's best features, with an abundance of passenger space, the 307 SSX is... View Details

Introducing the Regal Commodore 3860, a stunning cruiser that promises an exceptional boating experience. With an overall length of 40 feet, this vessel boasts a sleek design, ensu... View Details

See This stunning 2024 Cobalt R8 Outboard, a remarkable bowrider that combines elegance with performance. Measuring an impressive 27.83 feet in overall length, this vessel is craft... View Details

Powered by the PCM ZZ6 450hp direct-injection engine, this boat delivers the torque, precision, and responsiveness serious riders demand—along with the legendary reliability Nautiq... View Details

Experience the thrill of the water like never before with the 2025 Axis A245, designed for watersports enthusiasts who crave top-tier performance, comfort, and style. Powered by th... View Details

Complete with matching tandem axle trailer, this setup is perfect for wakeboarding, surfing, & creating unforgettable memories on the water.Powerful Performance: Equipped with the... View Details

Prepare for unparalleled excitement on the water with the 2024 Axis T220-r – a masterfully crafted vessel designed to elevate your watersport adventures to new heights. Packed with... View Details

Powered by the Malibu Monsoon M5Di engine, this 23.5-foot wake machine delivers the power, precision, and reliability you need to create massive, clean wakes and surf waves. Plus,... View Details

2025 Axis T250 with Matching Trailer – Zephyr Blue & WhiteTake your watersports experience to the next level with the all-new 2025 Axis T250, a 25-foot powerhouse designed for thos... View Details

Experience luxury, performance, and versatility with the 2025 Balise Horizon 24C Pontoon, designed for unforgettable days on the water. Powered by the robust Mercury 350 V10 Verado... View Details

Get ready to experience the perfect blend of agility, comfort, and cutting-edge features with this brand-new 2025 Cobalt CS22. Powered by an upgraded Volvo 280hp engine, this boat... View Details

Cobalt CS23 with Tidewater Trailer – Luxury, Power, and Style CombinedStep into luxury and performance with this stunning 2018 Cobalt CS23, now available for sale! This eye-catchin... View Details

Hit the water in style and power with the 2025 Cobalt CS23 Surf, designed for ultimate performance, comfort, and versatility. Powered by a forward-facing Volvo V8-300CE-G DP engine... View Details

Introducing the 2025 Cobalt CS23—a masterpiece of engineering and design that promises an exhilarating and luxurious ride.Powered by a powerful 280hp Volvo engine, the CS23 is read... View Details

2025 Cobalt R4—a boat that perfectly marries power, luxury, and style.Powered by a formidable 300hp Volvo engine, the R4 is engineered to provide an exhilarating experience on the... View Details