Boats for sale in Chicago Illinois

1,169 boats found within 100 miles out of 14,821 Boats Found

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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

$64,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 31' / 10'
- 2006 / Used
- $64,900
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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$64,900
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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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2019 Supra SA400

$115,000

Delavan, WI
- Delavan, WI
- Ski & Wake
- 25' / 0'
- 2019 / Used
- $115,000
Stock #360586 Reason for selling is "Plans changed". ANY and ALL offers will be put in front of our seller! Submit your offer today! 350HP INDMAR! TRAILER INCLUDED!! READY TO PL... View Details

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$115,000
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2016 Chaparral 290 Signature

$138,900

South Bend, IN
- South Bend, IN
- Cruiser
- 29' / 9'
- 2016 / Used
- $138,900
Stored Off Site, Shown By Appointment ONLY please! Most cruisers in this size range require you to wake up and disassemble the forward berth if you want to use the dinette for an... View Details

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$138,900
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1999 Sea Ray 500 Sundancer

$199,000

South Haven, MI
- South Haven, MI
- Express Cruiser
- 50' / 0'
- 1999 / Used
- $199,000
Stock #471094 Video of this vessel available at www [dot] popsells [dot] com/view/471094 Reason for selling is "Has not used enough". ANY and ALL offers will be put in front of... View Details

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$199,000
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2023 Custom Built 25 Hadlee Houseboat

$69,000

South Haven, MI
- South Haven, MI
- Houseboat
- 25' / 8'
- 2023 / Used
- $69,000
Custom Built Houseboat Immerse yourself in stylish and comfortable houseboat living with this newly built 2023 Hadley Houseboat, only the third one built, the other two have b... View Details

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$69,000
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2025 Yamaha 195S

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Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19' / 0'
- 2025 / New
- Call for price
Introducing the 2025 Yamaha 195S: Step into luxury and performance with the all-new 2025 Yamaha 195S. Crafted with precision and style, this boat is designed to elevate your time o... View Details

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2025 Mastercraft NXT20

$110,275

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20' / 0'
- 2025 / New
- $110,275
Explore the Waves in Style with the NXT20 Discover the perfect combination of affordability and excitement with the NXT20 boat. Measuring 20 feet, this sleek and stylish vessel is... View Details

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$110,275
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2025 Yamaha 195S

$52,621

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19' / 0'
- 2025 / New
- $52,621
Introducing the 2025 Yamaha 195S: Step into luxury and performance with the all-new 2025 Yamaha 195S. Crafted with precision and style, this boat is designed to elevate your time o... View Details

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$52,621
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2025 Cruisers 60 CANTIUS

$2,749,995

Pewaukee, WI
- Pewaukee, WI
- Yacht
- 60' / 0'
- 2025 / Used
- $2,749,995
Just Listed: 2025 Cruisers Yachts 60 Cantius – Brand New, Never Used Yacht. Fresh Water Boat! 5 Engine Hours! Trades Welcome and In House Financing is Available! Introducing an exc... View Details

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$2,749,995
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2025 Harris 230 Solstice

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Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 23' / 0'
- 2025 / New
- Call for price
Introducing the 2025 Harris 230 Solstice Luxury Redefined Step aboard the epitome of elegance and performance with the 2025 Harris 230 Solstice. Crafted with precision and attentio... View Details

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2025 Mastercraft NXT21

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Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 21' / 0'
- 2025 / New
- Call for price
Explore the Exciting NXT21 Boat The NXT21 is an exceptional vessel that combines luxury, convenience, and performance in one stunning package. Perfect for families looking to enhan... View Details

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2025 Harris 230 Cruiser

$68,858

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 23' / 0'
- 2025 / New
- $68,858
Experience Unmatched Adventure Introducing the 2025 Harris 230 Cruiser, where luxury meets performance on the water. Crafted for those who seek the perfect blend of excitement and... View Details

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$68,858
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2025 Harris 230 Cruiser

$68,768

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 23' / 0'
- 2025 / New
- $68,768
Luxurious Adventures Await with the 2025 Harris 230 Cruiser Embark on opulent escapades aboard the prestigious 2025 Harris 230 Cruiser, a symbol of elegance and performance. Unmatc... View Details

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$68,768
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2025 Harris 230 Cruiser

$70,232

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $70,232
Introducing the 2025 Harris 230 Cruiser - A Luxurious Escape on Water Immerse yourself in the epitome of luxury and performance with the 2025 Harris 230 Cruiser. Crafted with preci... View Details

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$70,232
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2025 Barletta CABRIO24UE

$88,359

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 21' / 0'
- 2025 / New
- $88,359
BARLETTA CABRIO 24 UE Is Cabrio right for you? Spend quality time with family on the water in the price-conscious Cabrio. Enjoy the same exceptional fit and finish, innovation, per... View Details

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$88,359
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