Boats for sale in Chicago Illinois

1,206 boats found within 100 miles out of 14,768 Boats Found

Back

Filter

2026 Barletta Cabrio 22 UC

Call for price

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 23' / 0'
- 2026 / New
- Call for price
Experience Luxury on Water Introducing the exquisite 2026 Barletta CABRIO22UC, where sophistication meets adventure. Crafted for those who cherish opulence, this vessel elevates yo... View Details

View 7 Photos and Details Contact Seller

Call for price
VIEW DETAILS
2026 Barletta Lusso 23 UC

Call for price

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 25' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Barletta LUSSO23UC Embark on unparalleled adventures with the stunning 2026 Barletta LUSSO23UC, where luxury meets performance. This new vessel, located at Ski... View Details

View 6 Photos and Details Contact Seller

Call for price
VIEW DETAILS
2026 Barletta Cabrio 22 QC

Call for price

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 23' / 0'
- 2026 / New
- Call for price
Experience Luxury on Water Introducing the 2026 Barletta CABRIO22QC, a stunning embodiment of craftsmanship and performance that will elevate your time on the water. Designed for d... View Details

View 7 Photos and Details Contact Seller

Call for price
VIEW DETAILS
Advertisement
2025 Sea Ray SLX 260

$182,956

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 25' / 0'
- 2025 / New
- $182,956
Take advantage of limited-time savings on in-stock boats!Act fast on this limited-time offer! Luxury Redefined: 2025 Sea Ray SLX 260 Sleek Elegance: The Sea Ray SLX 260, a 2025 mar... View Details

View 30 Photos and Details Contact Seller

$182,956
VIEW DETAILS
2000 Bayliner 5288 PILOTHOUSE MOTORHOUSE

$339,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 56' / 0'
- 2000 / Used
- $339,995
The "Live Aboard Lifestyle" simply does not get any better than this. Exclusively used in Fresh Water since new, this one owner Bayliner 5288 has been meticulously maintained since... View Details

View 30 Photos and Details Contact Seller

$339,995
VIEW DETAILS
1999 Trophy 2352FV

$14,995

Pewaukee, WI
- Pewaukee, WI
- Fishing
- 25' / 0'
- 1999 / Used
- $14,995
2019-Replaced Vinyl. 2016-Replaced Isenglas. Trades considered. View Details

View 9 Photos and Details Contact Seller

$14,995
VIEW DETAILS
1996 Sea Ray 270 SUNDANCER

$12,500

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 29' / 0'
- 1996 / Used
- $12,500
Introducing the 1996 Sea Ray 270 Sundancer - Where Luxury Meets Adventure. Experience the epitome of boating elegance with our meticulously crafted vessel, designed for those who d... View Details

View 30 Photos and Details Contact Seller

$12,500
VIEW DETAILS
Advertisement
Advertisement
2010 Sun Tracker PB20

$26,428

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20' / 0'
- 2010 / Used
- $26,428
2010 Sun Tracker PB20 - Set Sail in Luxury Experience the ultimate adventure on water with the 2010 Sun Tracker PB20, a vessel that perfectly blends performance and elegance. With... View Details

View 11 Photos and Details Contact Seller

$26,428
VIEW DETAILS
Advertisement
2016 Four Winns H200

$24,995

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 20' / 0'
- 2016 / Used
- $24,995
A well-kept 2016 Four Winns 200H outfitted with a Volvo Penta V6 225SX, 135hrs, Swim platform w/deep angled ladder, Swim platform lounge seats, Ski tow, iPod®/MP3 port AM/FM/Blueto... View Details

View 11 Photos and Details Contact Seller

$24,995
VIEW DETAILS
2009 Bennington 2575 RLI

$12,500

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2009 / Used
- $12,500
2009 Bennington 2575 RLI View Details

View 9 Photos and Details Contact Seller

$12,500
VIEW DETAILS
2025 Sea Ray SPX 190

Call for price

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 20' / 0'
- 2025 / New
- Call for price
Calling all water enthusiasts! Sea Ray has the answer to your boating dreams with the dynamic and affordable SPX 190. Designed for those who crave a premium on-water experience wit... View Details

View 30 Photos and Details Contact Seller

Call for price
VIEW DETAILS
2025 Yamaha 195S

Call for price

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

View 30 Photos and Details Contact Seller

Call for price
VIEW DETAILS
Advertisement
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

View 27 Photos and Details Contact Seller

$110,275
VIEW DETAILS
Advertisement
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

View 30 Photos and Details Contact Seller

$52,621
VIEW DETAILS
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

View 30 Photos and Details Contact Seller

$2,749,995
VIEW DETAILS
2025 Harris 230 Solstice

Call for price

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

View 16 Photos and Details Contact Seller

Call for price
VIEW DETAILS
2025 Mastercraft NXT21

Call for price

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

View 30 Photos and Details Contact Seller

Call for price
VIEW DETAILS
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

View 30 Photos and Details Contact Seller

$68,858
VIEW DETAILS
Advertisement
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

View 30 Photos and Details Contact Seller

$68,768
VIEW DETAILS
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

View 16 Photos and Details Contact Seller

$70,232
VIEW DETAILS
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

View 9 Photos and Details Contact Seller

$88,359
VIEW DETAILS