Boats for sale in Chicago Illinois

1,172 boats found within 100 miles out of 14,803 Boats Found

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2026 Sea Ray SLX 280 Outboard

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Walworth, WI
- Walworth, WI
- Cruiser
- 31' / 0'
- 2026 / New
- Call for price
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

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2026 Sea Ray SLX 350

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Walworth, WI
- Walworth, WI
- Runabout
- 36' / 0'
- 2026 / New
- Call for price
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

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2024 Robalo R250 Center Console

$186,446

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 25' / 9'
- 2024 / New
- $186,446
On Display Now, see this superbly equipped Robalo R250 Center Console. Featuring Robalo's latest design elements, the R250 is truly a big-water boat, with a nine-foot two-inch beam... View Details

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$186,446
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1990 Jefferson Marquessa 52

$219,900

Saint Joseph, MI
- Saint Joseph, MI
- Yacht
- 52' / 16'
- 1990 / Used
- $219,900
Classically-designed fresh-water motoryacht, now available! Three staterooms, three heads, split walk-in engine rooms, plus comfortable luxury in every direction. Gorgeous teak woo... View Details

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$219,900
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2023 Robalo R230 Center Console

$115,534

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 23' / 8'
- 2023 / New
- $115,534
In Stock! Gorgeous lines, updated to Robalo's latest styling design. Abundant passenger comfort with versatile seating and casting areas, fore and aft. Enclosed privacy compartment... View Details

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$115,534
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2006 Formula 330 Sun Sport

$94,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 33' / 10'
- 2006 / Used
- $94,900
If you are looking for a sporty, great performing, hot looking express cruiser, look no further! This Formula 330 Sun Sport is the perfect fit for your family's summer fun! Nicely... View Details

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$94,900
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2024 Robalo 226 Cayman

$106,934

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Bay / Flats / Skiff
- 22' / 8'
- 2024 / New
- $106,934
Now on Display, see this superbly equipped Robalo 226 Cayman! Powered by a 250 HP Mercury Four Stroke with Digital Throttle and Shift and matched with the most desirable options. I... View Details

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$106,934
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1995 Gibson 44 Classic

$79,900

Saint Joseph, MI
- Saint Joseph, MI
- Houseboat
- 44' / 14'
- 1995 / Used
- $79,900
See this well-loved and well-cared-for Gibson 44. "Lou's Yourself" has always been boated in fresh water, is beautifully decored and loaded with accessories. Twin Crusader 454's, W... View Details

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$79,900
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2024 Robalo R180 Center Console

$66,244

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 18' / 8'
- 2024 / New
- $66,244
On Display Now, see this Robalo R180 Center Console -- Loaded with our favorite factory options! Packed with features, durable quality and paired with Yamaha dependability. Enjoy... View Details

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$66,244
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2025 Robalo R202 Explorer

$83,728

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 20' / 8'
- 2025 / New
- $83,728
Robalo's R202 Explorer offers the convenience of a center console layout and ease of maintenance, plus expanded seating comfort for a full day of on-water family fun. Well-padded f... View Details

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$83,728
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2025 Robalo R160 Center Console

$41,430

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 16' / 7'
- 2025 / New
- $41,430
The R160 makes every on-water adventure more fun in a size that's easy to trailer and store. But don't think that it isn't designed with performance in-mind. Featuring the same on-... View Details

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$41,430
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2025 Chaparral 307 SSX

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Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30' / 9'
- 2025 / New
- Call for price
Now in stock! Step aboard one of Chaparral's most innovative designs - the spacious, sleek and powerful 307 SSX. With an abundance of comfortably contoured cockpit seating, lot of... View Details

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2004 Bayliner 245

$23,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 24' / 8'
- 2004 / Used
- $23,900
Bayliner's 245 Cruiser sports a comfortable cockpit and convenient cabin arrangement. The cockpit area includes a reversible portside companion seat -- converting from a forward fa... View Details

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$23,900
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2006 Chaparral 310 Signature

$69,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 31' / 10'
- 2006 / Used
- $69,900
This 2006 Chaparral 310 Signature is a sleek and luxurious cruiser designed for thosewho appreciate both performance and comfort on the water. With a length overall of 33 feet and... View Details

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$69,900
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1995 Sea Ray 400 Express Cruiser

$62,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 40' / 13'
- 1995 / Used
- $62,900
Nicely maintained fresh-water Sea Ray 400 Express. Twin Merc 454's with 537 engine hours, original. This classic express cruiser helped usher in the new era mid-'90's Sea Ray desig... View Details

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$62,900
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2002 Regal Commodore 3860

$114,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 40' / 13'
- 2002 / Used
- $114,900
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

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$114,900
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2024 Cobalt R8 Outboard

$219,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 27' / 8'
- 2024 / Used
- $219,900
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

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$219,900
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2007 Chaparral 350 Signature

$129,500

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 37' / 11'
- 2007 / Used
- $129,500
Always fresh-water, loaded with features. Twin Merc 8.1L 370 HP inboards with 460 hours. This is an ideal opportunity to own a well-cared-for Chaparral 350 Signature featuring a pr... View Details

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$129,500
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2024 Yamaha 252SE

$84,900

Saint Joseph, MI
- Saint Joseph, MI
- Jet boat
- 24' / 8'
- 2024 / Used
- $84,900
Check out this 2024 Yamaha Boats 252SE, a remarkable jet boat that combines performance and style. Powered by twin Yamaha 1.9L High Output inboard engines, each delivering an impre... View Details

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$84,900
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2005 Formula 260 Bowrider

$46,900

Saint Joseph, MI
- Saint Joseph, MI
- Runabout
- 26' / 8'
- 2005 / Used
- $46,900
Chase sunsets with this 2005 Formula 260 Bowrider, a premium sport boat built for performance, comfort, and luxury. A top brand known for its superior handling, quality constructio... View Details

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$46,900
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2018 Chaparral Vortex 203 VRX

$35,900

Saint Joseph, MI
- Saint Joseph, MI
- Jet boat
- 20' / 8'
- 2018 / Used
- $35,900
The 203 VRX features the hull design, interior layout and high quality construction Chaparral is known for. In addition to the head-turning style, the VRX includes a black folding... View Details

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$35,900
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