Boats for sale in Chicago Illinois

1,734 boats found within 100 miles from Chicago, Illinois

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2007 Cobalt 323

$89,900

Saint Joseph, MI
- Saint Joseph, MI
- Runabout
- 32' / 10'
- 2007 / Used
- $89,900
If you're in search of the perfect combination of luxury, performance, and offshore capabilities, look no further than this 2007 Cobalt 323. Cobalt is known for its sleek design an... View Details

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$89,900
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2023 Axis A20

$89,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 20' / 8'
- 2023 / Used
- $89,990
Get ready for endless thrills with this 2023 Axis A20, a top-tier wake boat built for performance, comfort, and style.Powered by the Malibu Monsoon M5Di 360hp engine and boasting o... View Details

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$89,990
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2017 Nautique Super Air Nautique G23

$89,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 23' / 102'
- 2017 / Used
- $89,990
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

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$89,990
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2016 Cobalt R7

$89,995

Antioch, IL
- Antioch, IL
- Cruiser
- 27' / 0'
- 2016 / Used
- $89,995
2016 Cobalt R7 View Details

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$89,995
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2022 Barletta LUSSO 23UCTT

$89,995

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2022 / Used
- $89,995
2022 Barletta LUSSO 23UCTT View Details

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$89,995
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2026 Starcraft SLS 3 Q DH

$90,076

Antioch, IL
- Antioch, IL
- Pontoon
- 23' / 0'
- 2026 / New
- $90,076
Act fast on this limited-time offer! Discover Unmatched Luxury on Water Experience the epitome of aquatic elegance with the 2026 Starcraft SLS-3 Q DH. This stunning vessel combines... View Details

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$90,076
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2026 Barletta Cabrio 22 UC

$93,049

Walworth, WI
- Walworth, WI
- Pontoon
- 23' / 0'
- 2026 / New
- $93,049
Is the Cabrio right for you? Spend time with family on the water in the price concious Cabrio. The same fit and finish, innovation, performance and superior construction that Barle... View Details

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$93,049
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2026 Barletta Cabrio 22 UC

$94,039

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2026 / New
- $94,039
Act fast on this limited-time offer! Experience Luxury on Water Introducing the exquisite 2026 Barletta CABRIO22UC, where sophistication meets adventure. Crafted for those who cher... View Details

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$94,039
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2026 Barletta Cabrio 22 U

$94,783

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2026 / New
- $94,783
Act fast on this limited-time offer! 2026 Barletta CABRIO22U Experience the allure of waterfront living with the stunning 2026 Barletta CABRIO22U, available exclusively at SkipperB... View Details

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$94,783
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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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2022 Cobalt CS23 Surf

$94,990

Fontana, WI
- Fontana, WI
- Bowrider
- 23' / 8'
- 2022 / Used
- $94,990
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$94,990
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2000 Hunter 410

$95,000

Racine, WI
- Racine, WI
- Sailboat
- 0' / 13'
- 2000 / Used
- $95,000
2000 Hunter 410 - "Cabaret" This Hunter has been maintained quite well over its life, kept on the Great Lake Michigan and moored at the Racine Yacht Club. Take your family sailing... View Details

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$95,000
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2026 Barletta Cabrio 22 U

$95,773

Walworth, WI
- Walworth, WI
- Pontoon
- 23' / 0'
- 2026 / New
- $95,773
Act fast on this limited-time offer! 2026 Barletta CABRIO22U Experience the allure of luxury on the water with the stunning 2026 Barletta CABRIO22U. This new vessel promises unmatc... View Details

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$95,773
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2025 Chaparral 23 SSi

$96,864

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23' / 8'
- 2025 / New
- $96,864
In Stock Now See the Chaparral 23 SSi, our best-selling 23-footer! This 23 SSi is superbly equipped with Mercury 300 HP Bravo 3 MPI power and many Chaparral extras. Trailer include... View Details

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$96,864
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2026 Barletta Cabrio 22 M

$97,116

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2026 / New
- $97,116
Act fast on this limited-time offer! 2026 Barletta CABRIO22M Experience the height of luxury and performance with the 2026 Barletta CABRIO22M, now available at SkipperBud's Pewauke... View Details

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$97,116
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2026 Barletta Cabrio 24 UE

$97,333

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $97,333
Is the Cabrio right for you/ Spend time with family on the water in the price sonscious Cabrio. The same fit and finish, innovation, performance adn superior construction that Barl... View Details

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$97,333
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2026 Barletta Cabrio 24 UE

$97,800

Walworth, WI
- Walworth, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $97,800
Act fast on this limited-time offer! Discover Elegance on Water Experience the allure of luxury boating with the 2026 Barletta CABRIO24UE, where sophistication meets adventure. Cra... View Details

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$97,800
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2021 Crownline 264 CR

$98,500

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 26' / 0'
- 2021 / Used
- $98,500
FRESHLY DETAILED, BUFFED & WAXED! Turn heads next season with this beautiful 2021 Crownline 264 CR — a perfect combination of luxury, performance, and comfort. With only 150 ho... View Details

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$98,500
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2022 Malibu 20VTX

$99,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 20' / 98'
- 2022 / Used
- $99,990
The 20 VTX is Malibu's ultimate triple threat. VTX stands for versatility and it truly is the boat that makes everyone happy whether you want to ski, wakesurf, or wakeboard. Its un... View Details

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$99,990
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2026 Barletta Cabrio 24 UE

$99,995

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $99,995
Act fast on this limited-time offer! Introducing the 2026 Barletta CABRIO24UE Experience unparalleled luxury on the water with the stunning 2026 Barletta CABRIO24UE. Designed with... View Details

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$99,995
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2021 Tige Z3

$99,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 23' / 0'
- 2021 / Used
- $99,995
2021 Tige Z3 View Details

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$99,995
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