Boats for sale in Chicago Illinois

1,752 boats found within 100 miles from Chicago, Illinois

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2026 Sea Ray SPX 210 Outboard

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Walworth, WI
- Walworth, WI
- Runabout
- 24' / 0'
- 2026 / New
- Call for price
Performance and fun. The reimagined 2026 Sea Ray SPX 210 Outboard is designed to be noticed, and delivers the next level of fun, perfect for hosting friends, sharing a casual cruis... View Details

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2026 Galeon 375 GTO

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Walworth, WI
- Walworth, WI
- Yacht
- 38' / 0'
- 2026 / New
- Call for price
Whether you like to race around in open water at 50 mph or raft up on a lazy Sunday afternoon, the 2026 Galeon 375 GTO is the boat for you. This sleek, sporty, and versatile cruise... View Details

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2026 Scout 305 LXF

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Walworth, WI
- Walworth, WI
- Fishing Center Console
- 30' / 0'
- 2026 / New
- Call for price
Step aboard the only 30-footer in its class with a console berth down below and optional air conditioning: Scout's 305 LXF. Enjoy the convenience of a removable bow table while enj... View Details

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2026 Scout 400 LXF Li-Ion

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Walworth, WI
- Walworth, WI
- Fishing Center Console
- 40' / 0'
- 2026 / New
- Call for price
The 2026 Scout 400 LXF Li-Ion is a new model and alternative version to the current 400 LXF, complete with a lithium ion battery management system (no generator necessary). These b... View Details

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2026 Sea Ray SPX 230 Outboard

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Walworth, WI
- Walworth, WI
- Runabout
- 26' / 0'
- 2026 / New
- Call for price
Powerful performance, agile handling. The 2026 Sea Ray SPX 230 Outboard is built to thrill. It combines the powerful performance and agile handling you'd expect from a world-class... View Details

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2004 Chaparral 280 SSi

$44,000

Waterford, WI
- Waterford, WI
- Bowrider
- 28' / 0'
- 2004 / Used
- $44,000
Stock #487201 Reason for selling is "Buying a smaller boat". This is a new advertisement, on the market just this week (Apr 20th). Always accepting offers! Large bowrider with t... View Details

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$44,000
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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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2021 Sylvan L3 LZ

$38,700

Edwardsburg, MI
- Edwardsburg, MI
- Pontoon
- 24' / 0'
- 2021 / Used
- $38,700
Stock #452780 Video of this vessel available at www [dot] popsells [dot] com/view/452780 Reason for selling is "Doesn't use it. Came with the home.". ANY and ALL offers will be... View Details

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$38,700
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2025 Mastercraft XSTAR

$354,977

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 23' / 0'
- 2025 / New
- $354,977
Act fast on this limited-time offer! Experience Unmatched Performance Introducing the 2025 Mastercraft XSTAR, where cutting-edge engineering meets exhilarating performance. This st... View Details

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$354,977
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2025 Harris 230 Cruiser

$49,300

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $49,300
Contact us to find out ALL available savings! Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line. No matter what you d... View Details

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$49,300
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2025 Harris 230 Cruiser

$49,867

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $49,867
Contact us to find out ALL available savings! Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line. No matter what you d... View Details

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$49,867
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2025 Mastercraft NXT22

$128,525

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 2025 / New
- $128,525
Contact us to find out ALL available savings! The fresh new MasterCraft NXT22 is big news. One of our most popular boats ever has a brand new design and updates from tip to tail. T... View Details

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$128,525
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2025 Harris 230 Cruiser

$50,187

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $50,187
Contact us to find out ALL available savings! Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line. No matter what you d... View Details

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$50,187
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2025 Sea Ray SDX 270

$182,584

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 27' / 0'
- 2025 / New
- $182,584
Contact us to find out ALL available savings! The SDX 270 delivers on maximum capability to make a full day on the water easy to enjoy. With plenty of seating, storage space and pr... View Details

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$182,584
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2025 Harris 210 Cruiser

$55,022

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $55,022
Contact us to find out ALL available savings! Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line. No matter what you d... View Details

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$55,022
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2025 Barletta LUSSO25UE

$135,131

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $135,131
Contact us to find out ALL available savings! BARLETTA LUSSO 25 UE Is Lusso right for you? Designed with you, and your on-water experience, in mind, the Barletta Lusso models offer... View Details

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$135,131
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2026 Barletta Corsa 25 UC

$133,243

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $133,243
Act fast on this limited-time offer! Discover the 2026 Barletta CORSA25UC Experience the pinnacle of luxury on the open water with the stunning 2026 Barletta CORSA25UC. This vessel... View Details

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$133,243
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2026 Starcraft SVX 211 OB

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Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 20' / 0'
- 2026 / New
- Call for price
Just landed and ready to make waves! Starcraft's SVX 211 OB fiberglass deck boat effortlessly combines the spaciousness of a deck boat with the agility of a ski boat, offering vers... View Details

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