Boats for sale in Chicago Illinois

1,585 boats found within 100 miles out of 14,269 Boats Found

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2026 Scarab SB 210 LX

$67,395

La Porte, IN
- La Porte, IN
- Jet boat Wakeboard
- 21'
- 2026 / New
- $67,395
2026 Scarab 210 LX – Bold Performance Meets Refined Comfort Step into the next evolution of jet boating with the all-new 2026 Scarab 210 LX. Engineered for adrenaline and styled fo... View Details

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$67,395
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2004 Baja 25 Outlaw

$41,000

Wonder Lake, IL
- Wonder Lake, IL
- Performance
- 25'
- 2004 / Used
- $41,000
Stock #389583 Video of this vessel available at www [dot] popsells [dot] com/view/389583 Reason for selling is "no longer using it.". ANY and ALL offers will be put in front of... View Details

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$41,000
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1997 Bayliner 2655 Ciera

$18,800

Harvard, IL
- Harvard, IL
- Express Cruiser
- 26'
- 1997 / Used
- $18,800
Stock #365912 Video of this vessel available at www [dot] popsells [dot] com/view/365912 ANY and ALL offers will be put in front of our seller! Submit your offer today! FRESH WA... View Details

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$18,800
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2024 Sea Doo 47RC SWITCH SPORT COMPACT

$26,500

Harvard, IL
- Harvard, IL
- Jet boat
- 17'
- 2024 / Used
- $26,500
Stock #485985 This is a new advertisement, on the market just this week (May 26th). Always accepting offers! 2024 SEA DOO 47RC SWITCH SPORT COMPACT JET BOAT INCLUDES KARAVAN TRAI... View Details

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$26,500
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2014 Chaparral 287 SSX

$74,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 28'
- 2014 / Used
- $74,900
Sharp, powerful Chaparral 287 SSX. Includes Volvo Penta 430 HP V-8 with DTS. Just 260 engine hours. Don’t miss out on this nicely maintained Chaparral 287 SSX. This 9-foot beam bo... View Details

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$74,900
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2016 Chaparral 287 SSX

$74,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 28'
- 2016 / Used
- $74,900
See this sharp, spacious fun machine, ready to take you to your favorite destinations. This 9-foot beam bow rider offers an abundance of comfortable passenger seating with a double... View Details

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$74,900
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2004 Bayliner 245

$23,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 24'
- 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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2017 Regal 2500 Bowrider

$69,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 26'
- 2017 / Used
- $69,900
This 2017 Regal 2500 Bowrider is the kind of boat that makes people suddenly volunteer to bring the snacks. Sleek, sporty, and loaded with Regal style and ready for her next captai... View Details

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$69,900
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2003 Chaparral 260 SSi

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 27'
- 2003 / Used
- $34,900
In our showroom now! If you are looking for a great value in today's boating market this is it! This lovingly cared for 260 SSi has only 543 freshwater hours on the Mercruiser 496... View Details

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$34,900
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2024 Robalo R250 Center Console

$186,446

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 25'
- 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'
- 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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2006 Formula 330 Sun Sport

$94,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 33'
- 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'
- 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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2024 Robalo R180 Center Console

$66,244

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 18'
- 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'
- 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'
- 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

Call for price

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30'
- 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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1995 Sea Ray 400 Express Cruiser

$62,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 40'
- 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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1996 Cruisers 3375 Rogue

$40,000

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 33'
- 1996 / Used
- $40,000
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

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$40,000
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2021 Chaparral 307 SSX

$149,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30'
- 2021 / Used
- $149,900
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

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$149,900
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2024 Cobalt R8 Outboard

$219,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 27'
- 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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