Boats for sale in Chicago Illinois

1,148 boats found within 100 miles out of 13,568 Boats Found

Back

Filter

Price Drop
2024 Cobalt R8 Outboard

$199,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 27'
- 2024 / Used
- $199,900
See This stunning 2024 Cobalt R8 Outboard, a remarkable bowrider that combines elegance with performance. Measuring an impressive 27.83 feet in overall length, this vessel is craft... View Details

View 48 Photos and Details Contact Seller

$199,900
VIEW DETAILS
2014 Chaparral 287 SSX

$74,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 28'
- 2014 / Used
- $74,900
Sharp, powerful Chaparral 287 SSX. Includes Volvo Penta 430 HP V-8 with DTS. Just 260 engine hours. Don’t miss out on this nicely maintained Chaparral 287 SSX. This 9-foot beam bo... View Details

View 31 Photos and Details Contact Seller

$74,900
VIEW DETAILS
2004 Bayliner 245

$23,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 24'
- 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

View 25 Photos and Details Contact Seller

$23,900
VIEW DETAILS
Advertisement
2007 Sweetwater SW 1986 RE-3 Gate

$10,900

Saint Joseph, MI
- Saint Joseph, MI
- Pontoon
- 19'
- 2007 / Used
- $10,900
Trailer Included! See this 2007 Sweetwater SW 1986 RE-3 Gate, an affordable pontoon boat that combines comfort and functionality. With an overall length of approximately 19.17 fee... View Details

View 25 Photos and Details Contact Seller

$10,900
VIEW DETAILS
2026 Chaparral 23 SSi

$89,259

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23'
- 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

View 44 Photos and Details Contact Seller

$89,259
VIEW DETAILS
2026 Chaparral 21 SSi OB

$75,794

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 21'
- 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

View 26 Photos and Details Contact Seller

$75,794
VIEW DETAILS
2026 Chaparral SSX 4

Call for price

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 24'
- 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

View 38 Photos and Details Contact Seller

Call for price
VIEW DETAILS
Advertisement
Advertisement
2026 Chaparral SSX 6

Call for price

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 26'
- 2026 / New
- Call for price
Look no further-the SSX 6 is breaking barriers and setting the standard for on-water comfort and performance. Equipped with a state-of-the-art oversized touchscreen display, the he... View Details

View 44 Photos and Details Contact Seller

Call for price
VIEW DETAILS
Advertisement
Price Drop
2018 Lund LX220 Pontoon

$37,500

Saint Joseph, MI
- Saint Joseph, MI
- Pontoon
- 23'
- 2018 / Used
- $37,500
Meet your ticket to endless summer fun on this 2018 Lund LX220 Tritoon. This Lund brings the perfect blend of power, comfort, and pure on-the-water fun. Powered by a 200HP Mercury... View Details

View 46 Photos and Details Contact Seller

$37,500
VIEW DETAILS
Price Drop
2002 Regal 3860

$104,999

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 38'
- 2002 / Used
- $104,999
Stock #467673 Reason for selling is "New Adventure!". This Regal has been on the market for more than 30 days (May 1st). If you are thinking of making an offer, submit it today a... View Details

View 10 Photos and Details Contact Seller

$104,999
VIEW DETAILS
1999 Trojan 360 Express

$68,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 36'
- 1999 / Used
- $68,900
Spacious and Sporty, this Trojan (by Carver) 360 Express is the perfect family boat for cruising and enjoying the water! It is equipped with a Kohler generator for those hot summer... View Details

View 32 Photos and Details Contact Seller

$68,900
VIEW DETAILS
2002 Maxum 2700 SCR

$32,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 28'
- 2002 / Used
- $32,900
This one-owner 2002 Maxum 2700 SCR has spent its life on the fresh waters of Southwest Michigan and shows the care you hope to find in a well-kept family cruiser. With sleek stylin... View Details

View 49 Photos and Details Contact Seller

$32,900
VIEW DETAILS
Advertisement
2006 Chaparral 310 Signature

$64,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 31'
- 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

View 35 Photos and Details Contact Seller

$64,900
VIEW DETAILS
Advertisement
2022 Robalo R242 Explorer

$119,900

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 24'
- 2022 / Used
- $119,900
This Freshwater only Robalo 242 Explorer is at the top of it's class and for good reason. This 24 foot platform is the pinnacle of what the Explorer series is all about. Providing... View Details

View 50 Photos and Details Contact Seller

$119,900
VIEW DETAILS
1996 Monterey 276

$24,000

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 27'
- 1996 / Used
- $24,000
Stock #494642 This is a new advertisement, on the market just this week (Jun 16th). Always accepting offers! Featuring new seats and flooring in aft. Boat has a double bimini wit... View Details

View 10 Photos and Details Contact Seller

$24,000
VIEW DETAILS
2022 Other Nepallo 22 QL

$29,900

Saint Joseph, MI
- Saint Joseph, MI
- Pontoon
- 22'
- 2022 / Used
- $29,900
Hit the water now with this 2022 Nepallo 22QL tritoon, the perfect blend of performance, comfort, and style. Powered with a 115HP Suzuki for smooth cruising and equipped with a tri... View Details

View 33 Photos and Details Contact Seller

$29,900
VIEW DETAILS
2006 Sea Ray 270 Sundeck

$32,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 26'
- 2006 / Used
- $32,900
Fresh to the Southern Lake Michigan market, this 2006 Sea Ray 270 Sundeck is a spacious and versatile deck boat designed for entertaining, cruising, and making the most of your tim... View Details

View 40 Photos and Details Contact Seller

$32,900
VIEW DETAILS
1999 Sea Ray 290 Sundancer

$42,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 29'
- 1999 / Used
- $42,900
This 1999 Sea Ray 290 Sundancer is the perfect blend of weekend cruiser, sunset chaser, and floating cottage. Powered by twin mercury engines, this popular express cruiser offers t... View Details

View 51 Photos and Details Contact Seller

$42,900
VIEW DETAILS
Advertisement
2007 Chaparral 350 Signature

$129,500

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 37'
- 2007 / Used
- $129,500
Always fresh-water, loaded with features. Twin Merc 8.1L 370 HP inboards with 460 hours. This is an ideal opportunity to own a well-cared-for Chaparral 350 Signature featuring a pr... View Details

View 35 Photos and Details Contact Seller

$129,500
VIEW DETAILS
2005 Formula 260 Bowrider

$46,900

Saint Joseph, MI
- Saint Joseph, MI
- Runabout
- 26'
- 2005 / Used
- $46,900
Chase sunsets with this 2005 Formula 260 Bowrider, a premium sport boat built for performance, comfort, and luxury. A top brand known for its superior handling, quality constructio... View Details

View 31 Photos and Details Contact Seller

$46,900
VIEW DETAILS
Price Drop
2018 Chaparral Vortex 203 VRX

$32,900

Saint Joseph, MI
- Saint Joseph, MI
- Jet boat
- 20'
- 2018 / Used
- $32,900
The 203 VRX features the hull design, interior layout and high quality construction Chaparral is known for. In addition to the head-turning style, the VRX includes a black folding... View Details

View 42 Photos and Details Contact Seller

$32,900
VIEW DETAILS