Boats for sale in Chicago Illinois

Let’s talk about pre-qualifying for a boat loan

Boat ownership has never been more affordable or easier. Whether you are looking to purchase a new boat or refinance your existing loan, we can help.

Back

Filter

2026 Harris 230 CRUISER

$81,392

Coopersville, MI
- Coopersville, MI
- Pontoon
- 23' / 8'
- 2026 / New
- $81,392
2026 Harris 230 CRUISERHIN: HAMP6157K526 View Details

View 3 Photos and Details Contact Seller

$81,392
VIEW DETAILS
1953 Chris Craft 24 Express Cruiser

$27,900

Hickory Corners, MI
- Hickory Corners, MI
- Classic / Antique
- 24' / 0'
- 1953 / Used
- $27,900
Stock #315119 Reason for selling is "Phasing out". ANY and ALL offers will be put in front of our seller! Submit your offer today! CLASSIC, CHRIS CRAFT EXPRESS CRUISER IN GREAT... View Details

View 10 Photos and Details Contact Seller

$27,900
VIEW DETAILS
2020 Malibu 23MXZ

$99,995

Madison, WI
- Madison, WI
- Ski & Wake
- 23' / 0'
- 2020 / Used
- $99,995
You and your Family will enjoy a day on the lake with this well cared for 2020 Malibu 23 MXZ. This boat was always kept inside. If you are looking for one of the best wakeboard boa... View Details

View 30 Photos and Details Contact Seller

$99,995
VIEW DETAILS
Advertisement
2018 Yamaha 212X

$39,995

Madison, WI
- Madison, WI
- Jet boat
- 21' / 0'
- 2018 / Used
- $39,995
You and your Family will enjoy a nice day on the lake with this 2018 Yamaha 212X Jet boat. This one comes with the ballast tanks for surfing and wakeboarding. If you are looking fo... View Details

View 20 Photos and Details Contact Seller

$39,995
VIEW DETAILS
2019 Scarab 215/ID

$29,995

Madison, WI
- Madison, WI
- Jet boat
- 21' / 0'
- 2019 / Used
- $29,995
You and your Family will enjoy a day on the lake with this 21 ft Scarab jet boat. Comes with a bunk trailer as well. If you are looking for a fun toy here it is. Financing Availabl... View Details

View 15 Photos and Details Contact Seller

$29,995
VIEW DETAILS
2000 Sea Ray 185 BR

$7,995

Madison, WI
- Madison, WI
- Bowrider
- 18' / 0'
- 2000 / Used
- $7,995
Looking for a budget bowrider for your first boat? Then this is the boat for you! Good condition for the year with low hours and the carpet and covers are in great condition. Power... View Details

View 24 Photos and Details Contact Seller

$7,995
VIEW DETAILS
2020 Beneteau ANTARES 27

$189,995

Madison, WI
- Madison, WI
- Cruiser
- 27' / 0'
- 2020 / Used
- $189,995
This is an express cruiser design. With twin Mercury 200 V6 outboards, it delivers impressive performance, a reassuring and comfortable ride, and a level of versatility that will e... View Details

View 28 Photos and Details Contact Seller

$189,995
VIEW DETAILS
Advertisement
Advertisement
2005 Nautique 211 LTD

$19,995

Madison, WI
- Madison, WI
- Ski & Wake
- 21' / 0'
- 2005 / Used
- $19,995
Enjoy water sports all summer with friends and family. Tubing, skiing, wake boarding or just cruising. Get ready for the season! Trades considered. View Details

View 11 Photos and Details Contact Seller

$19,995
VIEW DETAILS
Advertisement
Price Drop
2025 Bayliner VR4

$43,752

Madison, WI
- Madison, WI
- Bowrider
- 18' / 0'
- 2025 / New
- $43,752
Act fast on this limited-time offer! The latest in our VR Series of highly evolved bowriders the VR4 is easy to tow launch and store and really fun to use. The smallest VR Series m... View Details

View 11 Photos and Details Contact Seller

$43,752
VIEW DETAILS
2024 Harris Cruiser 230

Call for price

Madison, WI
- Madison, WI
- Pontoon
- 25' / 0'
- 2024 / New
- Call for price
Contact us to find out ALL available savings! Take advantage of limited-time savings on in-stock boats!HARRIS 230 CRUISERS CWDH All Sale and/or Clearance Prices include all rebates... View Details

View 23 Photos and Details Contact Seller

Call for price
VIEW DETAILS
2024 Yamaha 195AR

$43,265

Madison, WI
- Madison, WI
- Jet boat
- 19' / 8'
- 2024 / New
- $43,265
Contact us to find out ALL available savings! With its supercharged engine, innovative design and watersports features, the AR195 is ready for anything you throw at it. View Details

View 8 Photos and Details Contact Seller

$43,265
VIEW DETAILS
2024 Sylvan MIRAGE 8524

$46,096

Madison, WI
- Madison, WI
- Pontoon
- 24' / 9'
- 2024 / New
- $46,096
Contact us to find out ALL available savings! SYLVAN 8524 MIR LZ All Sale and/or Clearance Prices include all rebates and incentives. View Details

View 14 Photos and Details Contact Seller

$46,096
VIEW DETAILS
Advertisement
2025 Sea Ray 250 SDX

$161,173

Madison, WI
- Madison, WI
- Cruiser
- 25' / 0'
- 2025 / New
- $161,173
Take advantage of limited-time savings on in-stock boats!Immerse in Luxury: 2025 Sea Ray SDX 250 Performance: Experience the thrill of cruising on the water with the Sea Ray SDX 25... View Details

View 30 Photos and Details Contact Seller

$161,173
VIEW DETAILS
Advertisement
2026 Barletta Cabrio 24 UE

Call for price

Madison, WI
- Madison, WI
- Other / Not Classified
- 25' / 0'
- 2026 / New
- Call for price
Experience Luxury on the Water Discover the epitome of elegance and performance with the 2026 Barletta CABRIO24UE, available exclusively at SkipperBud's Madison in Madison, WI. Thi... View Details

View 10 Photos and Details Contact Seller

Call for price
VIEW DETAILS
2025 Barletta Cabrio

$83,188

Madison, WI
- Madison, WI
- Pontoon
- 22' / 0'
- 2025 / New
- $83,188
BARLETTA CABRIO 22 UC Luxury Redefined: 2025 Barletta Cabrio22UCTT Step into a world of luxury and performance with the 2025 Barletta Cabrio22UCTT. Crafted to perfection with exqui... View Details

View 30 Photos and Details Contact Seller

$83,188
VIEW DETAILS
2025 Yamaha 222S

$78,003

Madison, WI
- Madison, WI
- Cruiser
- 22' / 0'
- 2025 / New
- $78,003
Act fast on this limited-time offer! Sale Price: $78,787 All Sale and/or Clearance Prices include all rebates and incentives. Combining watersports capabilities with innovative des... View Details

View 30 Photos and Details Contact Seller

$78,003
VIEW DETAILS
2025 Barletta Cabrio

$77,864

Madison, WI
- Madison, WI
- Pontoon
- 22' / 0'
- 2025 / New
- $77,864
Act fast on this limited-time offer! BARLETTA CABRIO 22 QC Is Cabrio right for you? Spend time with family on the water in the price conscious Cabrio. The same fit and finish, inno... View Details

View 26 Photos and Details Contact Seller

$77,864
VIEW DETAILS
2025 Barletta Cabrio

$76,572

Madison, WI
- Madison, WI
- Pontoon
- 22' / 0'
- 2025 / New
- $76,572
Act fast on this limited-time offer! BARLETTA CABRIO 22 QC Is Cabrio right for you? Spend time with family on the water in the price conscious Cabrio. The same fit and finish, inno... View Details

View 26 Photos and Details Contact Seller

$76,572
VIEW DETAILS
Advertisement
2025 Sylvan MIRAGE 8522

$45,716

Madison, WI
- Madison, WI
- Pontoon
- 22' / 0'
- 2025 / New
- $45,716
Act fast on this limited-time offer! SYLVAN 8522 MIR LZ Introducing the 2025 Sylvan 8522 Mirage LZ Elevate your boating experience with the epitome of luxury and innovation. Perfor... View Details

View 24 Photos and Details Contact Seller

$45,716
VIEW DETAILS
2025 Starcraft EXS 3 TT

$60,175

Madison, WI
- Madison, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $60,175
Act fast on this limited-time offer! This 2025 Starcraft EXS3TT is Starcraft's EXS series that puts third-tube performance within the reach of every family. With a full load of pre... View Details

View 17 Photos and Details Contact Seller

$60,175
VIEW DETAILS
2025 Starcraft EXS 3 Q DH TT

$68,671

Madison, WI
- Madison, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $68,671
Act fast on this limited-time offer! This 2025 Starcraft EXS3QDHTT is Starcraft's EXS series that puts third-tube performance within the reach of every family. With a full load of... View Details

View 5 Photos and Details Contact Seller

$68,671
VIEW DETAILS