Boats for sale in Chicago Illinois

Introducing the 2026 Cruisers Yachts 38 GLS. With a drop-down beach door, hydraulic swim platform, and spacious bow lounge, the 38 GLS I/O for sale near you brings your day boating... View Details

Step aboard the pinnacle of maritime luxury where tranquility and timelessness converge seamlessly. From the expansive master suite to the gorgeous VIP stateroom, every corner of t... View Details

The 2026 Cruisers Yachts 38 GLS Outboard combines the unmatched performance and entertainment capabilities of the 38 GLS with powerful, easy-to-maintain outboards. Expand your swim... View Details

Handcrafted American legacy. With a rich history and unrivaled passion, Cruisers Yachts creates American-made boats for the world. With 360 degree windows and an open-plan main dec... View Details

The 2026 Cruisers Yachts 34 GLS Outboard for sale near you offers all of the excitement of the 34 GLS I/O with the unsurpassed ease of maintenance of outboard engines. THe 34 GLS'... View Details

Navigate waters with ease in the 2026 Crusiers Yachts 42 GLS. Powered by Mercury engines reach speeds up to 48 mph. With dual beach doors, a full galley, comfortable seating, and s... View Details

Introducing the 2025 Mastercraft XT25 Step aboard the epitome of luxury and performance with the Mastercraft XT25, a true marvel on the water. Luxurious Craftsmanship Crafted with... View Details

The 2026 Cruisers Yachts 34 GLS inboard includes open bow seating, a spacious cockpit with galley, and joystick piloting allowing you to navigate at speeds up to 47 mph. Feel the p... View Details

Orchestrated excellence. The 2026 Sea Ray's SLX 400 Outboard, "The Entertainer", is an outboard variant of the Innovation Award-winning SLX 400, with massive capacity, deluxe ameni... View Details

True leisure and maximum comfort. The 2026 Sea Ray SDX 250 Outboard is built for true leisure and comfort. With exceptional storage space, enhanced ergonomic seating, and dual 9" d... View Details

Share the thrill. Expansive social areas, a standard wet bar and plenty of available seating means hosting friends and family has been more comfortable. Aboard the 2026 Sea Ray SLX... View Details

Introducing the 2026 Sea Ray SLX 350 Outboard, luxury elevated. The SLX 350 Outboard incorporates top SLX features and enhancements that set the standard for large dayboats. The SL... View Details

The 2026 Sea Ray SLX 310: Luxury and Style Redefined. The 2026 Sea Ray SLX 310 sets the standard for luxury and style on the water. This exceptional boat combines cutting-edge desi... View Details

Adventure awaits with the 2026 Sea Ray SLX 400. Winner of an NMMA Innovation Award, Sea Ray's SLX 400, the "The Entertainer", combines peak performance, superior comfort, incredibl... View Details

Head turning elegance. Make your ultimate getaway in the 2026 Sea Ray SLX 280. Excluding luxury in a single glance, the elegant vessel showcases peak performance, impeccable style... View Details

Introducing the 2026 Sea Ray SLX 280 Outboard. Experience luxury and performance like never before with the Sea Ray SLX 280 Outboard. This stylish and modern boat is designed to el... View Details

Luxury elevated. Sea Ray's SLX 350 hosts an array of features designed for an excellent on-water experience and optimal performance. Powered by twin Mercury MerCruiser 6.2L engines... View Details

2023 GALA Viking V330Honda BF30D3LRTTrailmaster CR1515V330 Boat Specs:• LOA: 10'10"• Beam: 5'8"• Bare Boat Weight: 275 lbs• Loading Capacity: 1100 lbs / 5 Persons• Engine Max: 30 H... View Details

1993 Catalina 42 MKIThis vessel is equipped with a Dodger, Bimini and connector. Refrigerator, VHF, Stereo System have been upgraded. An AIS system and Garmin GPS/Depth Sounder has... View Details

2023 Robalo 266 Cayman - Deepwater BlackMercury Verado DTS 400XXLCoyote Tandem Axle Aluminum Trailer266 Cayman Unique Key Features:• 2 Passenger Flip-up Transom w/ High Backrest• 3... View Details

2025 Robalo R250 - In Stock!Twin Mercury DTS 200XLCoyote Aluminum Tandem Axle TrailerStandard Factory Options Included With this Package:• Solid Hull Alloy Gray Gel Coat• Cockpit I... View Details