Boats for sale in Chicago Illinois

1,734 boats found within 100 miles from Chicago, Illinois

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1994 Pacific Seacraft 34

$100,000

Racine, WI
- Racine, WI
- Sailboat
- 0' / 10'
- 1994 / Used
- $100,000
1994 Pacific Seacraft 34 "Esmerelda" This William Crealock designed 1994 Pacific Seacraft cutter is ready for your next sailing adventure. The vessel has been stored indoors thro... View Details

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$100,000
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2025 Harris 230 Solstice

$101,543

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $101,543
Contact us to find out ALL available savings! Introducing the 2025 Harris 230 Solstice Luxury Redefined Step aboard the epitome of elegance and performance with the 2025 Harris 230... View Details

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$101,543
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2026 Robalo Explorer R232EX

$101,855

Racine, WI
- Racine, WI
- Performance
- 23' / 8'
- 2026 / New
- $101,855
Set sail in style with the 2026 Robalo Explorer R232EX. This sleek center console boat is a true beauty on the water, available in a variety of stunning colors including Alloy Gray... View Details

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$101,855
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2026 Barletta Cabrio 24 QC

$102,637

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $102,637
2026 Barletta CABRIO24QC Experience the epitome of aquatic luxury with the 2026 Barletta CABRIO24QC, now available at SkipperBud's Pewaukee in Pewaukee, WI. This stunning vessel re... View Details

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$102,637
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2023 Malibu Response TXi

$105,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 21' / 95'
- 2023 / Used
- $105,990
Step into world-class waterskiing performance with this very gently used 2023 Malibu Response TXi, complete with a matching trailer. Known as the pinnacle of precision in the water... View Details

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$105,990
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2020 Mastercraft X22

$106,421

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 2020 / Used
- $106,421
The X22 is an absolute surf beast and has a wave that is right for everyone. Whether you are a surf enthusiast, or just a weekend warrior, the X22 won't disappoint. Give us a call... View Details

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$106,421
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2024 Robalo 226 Cayman

$106,934

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Bay / Flats / Skiff
- 22' / 8'
- 2024 / New
- $106,934
Now on Display, see this superbly equipped Robalo 226 Cayman! Powered by a 250 HP Mercury Four Stroke with Digital Throttle and Shift and matched with the most desirable options. I... View Details

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$106,934
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2026 Barletta Cabrio 24 M

$108,131

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $108,131
Act fast on this limited-time offer! 2026 Barletta CABRIO24M: Elevate Your Adventure Discover the epitome of luxury on the water with the all-new 2026 Barletta CABRIO24M, proudly o... View Details

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$108,131
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2026 Barletta Cabrio 24 UC

$108,157

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $108,157
2026 Barletta CABRIO24UC Discover the exceptional 2026 Barletta CABRIO24UC, a luxury vessel that epitomizes sophistication and adventure on the water. Located at SkipperBud's Pewau... View Details

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$108,157
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2026 Yamaha 252S

$108,310

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 25' / 0'
- 2026 / New
- $108,310
Act fast on this limited-time offer! Experience the Ultimate Luxury on Water Step aboard the 2026 Yamaha 252S, where unparalleled performance meets exquisite craftsmanship. This ne... View Details

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$108,310
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2002 Regal 3860

$109,000

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 38' / 0'
- 2002 / Used
- $109,000
Stock #467673 This is a new advertisement, on the market just this week (May 1st). Always accepting offers! Incredible luxury, performance, and a sound system that will make you... View Details

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$109,000
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2025 Mastercraft NXT20

$109,114

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20' / 8'
- 2025 / New
- $109,114
Contact us to find out ALL available savings! Explore the Waves in Style with the NXT20 Discover the perfect combination of affordability and excitement with the NXT20 boat. Measur... View Details

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$109,114
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2025 Mastercraft NXT20

$109,114

Antioch, IL
- Antioch, IL
- Ski & Wake
- 20' / 0'
- 2025 / New
- $109,114
Contact us to find out ALL available savings! Explore the Waves in Style with the NXT20 Discover the perfect combination of affordability and excitement with the NXT20 boat. Measur... View Details

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$109,114
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2026 Barletta Cabrio 24 UE

$109,624

Antioch, IL
- Antioch, IL
- Pontoon
- 25' / 0'
- 2026 / New
- $109,624
Act fast on this limited-time offer! 2026 Barletta CABRIO24UE: A New Standard in Luxury Step aboard the 2026 Barletta CABRIO24UE and experience the epitome of luxury on water. This... View Details

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$109,624
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2025 Robalo R230

$109,950

Racine, WI
- Racine, WI
- Performance
- 23' / 8'
- 2025 / New
- $109,950
2025 Robalo R230 - Solid White Mercury 250XL Factory Options Included With this Package: - White Hull - Cockpit Interior - Harbor Black - Canvas Color - Black (If Equipped) - Ca... View Details

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$109,950
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2025 Mastercraft NXT20

$110,275

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20' / 0'
- 2025 / New
- $110,275
Contact us to find out ALL available savings! Explore the Waves in Style with the NXT20 Discover the perfect combination of affordability and excitement with the NXT20 boat. Measur... View Details

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$110,275
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2026 Barletta Cabrio 24 UE

$110,389

Walworth, WI
- Walworth, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $110,389
Is the Cabrio right for you/ Spend time with family on the water in the price sonscious Cabrio. The same fit and finish, innovation, performance adn superior construction that Barl... View Details

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$110,389
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2025 Barletta CORSA23QCSS

$110,581

Antioch, IL
- Antioch, IL
- Pontoon
- 23' / 0'
- 2025 / New
- $110,581
Contact us to find out ALL available savings! BARLETTA CORSA 23 QC SS Is the Corsa right for you? Built for those who want everything that makes Barletta great, with a sporty, aggr... View Details

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$110,581
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2026 Barletta Cabrio 24 UE

$110,593

Antioch, IL
- Antioch, IL
- Pontoon
- 25' / 0'
- 2026 / New
- $110,593
Is the Cabrio right for you/ Spend time with family on the water in the price sonscious Cabrio. The same fit and finish, innovation, performance adn superior construction that Barl... View Details

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$110,593
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2025 Barletta LUSSO23UC

$114,732

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $114,732
Contact us to find out ALL available savings! BARLETTA LUSSO 25 UC 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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$114,732
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2007 Hunter 38

$114,900

Racine, WI
- Racine, WI
- Sailboat
- 0' / 12'
- 2007 / Used
- $114,900
2007 Hunter 38 Available for viewing!! Overview If you’ve been waiting for the right cruising sailboat—this is it. This 2007 Hunter 38 delivers the perfect combination of perfo... View Details

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$114,900
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