Boats for sale in Chicago Illinois - BoatCrazy

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2016 Chaparral 287 SSX

$74,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 28' / 0'
- 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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1999 Sea Ray 370 Express Cruiser

$79,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 41' / 0'
- 1999 / Used
- $79,900
Available and on display! The superbly designed 370 Express Cruiser features the full realm of Sea Ray luxuries, plus desirable characteristics unique to the EC series -- expansive... View Details

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$79,900
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2026 Chaparral 23 SSi

$89,259

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23' / 8'
- 2026 / New
- $89,259
Everything that has made Chaparral's wildly popular SSi Series the talk of the waterways, gets bigger and better with the amazing 23 SSi. With a ChaparralONE price including the tr... View Details

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$89,259
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2026 Chaparral 21 SSi OB

$75,794

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 21' / 8'
- 2026 / New
- $75,794
Now on display, see this new 2026 Chaparral 21 SSi powered by a hearty 200 HP Yamaha 4-stroke outboard. Chaparral's innovative use of space means an abundance of cockpit space, sto... View Details

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$75,794
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2026 Chaparral 21 SSi

$73,189

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 21' / 8'
- 2026 / New
- $73,189
See this New 2026 Chaparral 21 SSi! How much fun can you pack into one summer? Plenty, aboard your new Chaparral. Trailerable to your favorite destinations. Nimble, efficient and p... View Details

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$73,189
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2026 Chaparral SSX 4

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Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 24' / 8'
- 2026 / New
- Call for price
The SSX 4 packs more elegance, performance, and innovation than boaters have ever experienced at this widely popular length. Its stylish lines, meticulous attention to detail, and... View Details

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2017 Chaparral 21 H2O Ski & Fish

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Fish & Ski
- 21' / 8'
- 2017 / Used
- $34,900
Sold new @ Pier 33 in 2017 this boat has lived on its factory trailer and has been garaged since its purchase! With very low freshwater only hours on the motor this little runabout... View Details

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$34,900
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2003 Chaparral 260 SSi

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 27' / 0'
- 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 Chaparral 267 SSX

$140,000

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 26' / 0'
- 2024 / Used
- $140,000
Currently Inside Heated Storage, More Pictures To Come In Spring! The Chaparral 267 SSX is breaking barriers and setting the standard in quality. Equipped with state of the art du... View Details

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$140,000
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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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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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2025 Harris 230 Cruiser

$68,001

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 23' / 0'
- 2025 / New
- $68,001
Introducing the 2025 Harris 230 Cruiser Embark on a journey of luxury and adventure with the exquisite 2025 Harris 230 Cruiser. Crafted for those who seek the utmost in performance... View Details

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$68,001
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Showing 799 to 819 of 1,169 boats found.

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