Boats for sale in Chicago Illinois

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

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2025 Barletta LUSSO23M

$147,979

Antioch, IL
- Antioch, IL
- Pontoon
- 25' / 0'
- 2025 / New
- $147,979
Contact us to find out ALL available savings! BARLETTA LUSSO 23 M 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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$147,979
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2021 Chaparral 307 SSX

$149,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30' / 9'
- 2021 / Used
- $149,900
One-Owner, Fresh-Water, rack-stored Chaparral 307 SSX. Plushness and Performance! Loaded with all of Chaparral's best features, with an abundance of passenger space, the 307 SSX is... View Details

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$149,900
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2022 Mastercraft X22

$149,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 2022 / Used
- $149,995
The 2022 MasterCraft X22 is a high-performance wake boat that delivers premium features and serious on-the-water fun—without the full cost of buying new. As a late-model, used boat... View Details

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$149,995
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2026 Barletta Lusso 23 U

$150,123

Antioch, IL
- Antioch, IL
- Pontoon
- 25' / 0'
- 2026 / New
- $150,123
Act fast on this limited-time offer! 2026 Barletta LUSSO23U Discover exceptional luxury on water with the 2026 Barletta LUSSO23U, available now at SkipperBud's Antioch in Antioch,... View Details

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$150,123
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2026 Robalo Cayman 266

$151,055

Racine, WI
- Racine, WI
- Fishing Center Console
- 26' / 9'
- 2026 / New
- $151,055
Step on board the captivating 2026 Robalo Cayman 266 - a stunning center console boat that is sure to turn heads on the water. This sleek vessel is available in a variety of colors... View Details

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$151,055
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2026 Barletta Lusso 25 U

$151,055

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 27' / 0'
- 2026 / New
- $151,055
Act fast on this limited-time offer! Discover the Elegance of Luxury Experience the pinnacle of aquatic opulence with the 2026 Barletta LUSSO25U, now available at SkipperBud's Pewa... View Details

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$151,055
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2026 Barletta Lusso 23 QCSS

$153,042

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- $153,042
Act fast on this limited-time offer! Experience the Exhilaration The 2026 Barletta LUSSO23QCSS is more than just a boat; it's your ticket to unforgettable adventures on the water.... View Details

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$153,042
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2025 Axis T250

$153,624

Fontana, WI
- Fontana, WI
- Ski & Wake
- 25' / 8'
- 2025 / New
- $153,624
2025 Axis T250 with Matching Trailer – Zephyr Blue & WhiteTake your watersports experience to the next level with the all-new 2025 Axis T250, a 25-foot powerhouse designed for thos... View Details

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$153,624
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2026 Barletta Lusso 23 M

$157,301

Antioch, IL
- Antioch, IL
- Pontoon
- 25' / 0'
- 2026 / New
- $157,301
Act fast on this limited-time offer! Indulge in Luxury Experience the epitome of elegance with the 2026 Barletta LUSSO23M, a vessel that redefines luxury on water. At SkipperBud's... View Details

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$157,301
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2019 Beneteau Oceanis 35.1

$159,900

Racine, WI
- Racine, WI
- Sailboat
- 0' / 12'
- 2019 / Used
- $159,900
2019 Beneteau Oceanis 35.1 | Freshwater | Turnkey If you’ve been searching for a late-model cruising sailboat in the 35–36 ft range, you already know how competitive this segment... View Details

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$159,900
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2023 Malibu 24 MXZ

$159,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 24' / 8'
- 2023 / Used
- $159,990
Powered by the M6Di Monsoon engine, this 24MXZ delivers massive torque, smooth acceleration, & the muscle needed to build world-class waves. Equipped with Surf Gate & the Malibu Su... View Details

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$159,990
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2023 Malibu 25 LSV

$160,390

Fontana, WI
- Fontana, WI
- Ski & Wake
- 25' / 8'
- 2023 / Used
- $160,390
2023 Malibu 25 LSV, the ultimate luxury wakeboarding and surfing machine. This stunning boat is equipped with a powerful M6Di engine, producing a whopping 430 horsepower, making it... View Details

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$160,390
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2006 Sea Ray 38 Sundancer

$169,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 39' / 0'
- 2006 / Used
- $169,000
Just listed! The timeless lines of the 2005-2010 Sea Ray Sundancer units can't be mistaken, and this all fresh water gem has many more wonderful years remaining to help provide her... View Details

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$169,000
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2025 Balise Horizon 24C

$169,990

Fontana, WI
- Fontana, WI
- Pontoon
- 24' / 8'
- 2025 / New
- $169,990
Experience luxury, performance, and versatility with the 2025 Balise Horizon 24C Pontoon, designed for unforgettable days on the water. Powered by the robust Mercury 350 V10 Verado... View Details

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$169,990
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2025 Cobalt CS23 Surf

$170,391

Fontana, WI
- Fontana, WI
- Ski & Wake
- 23' / 8'
- 2025 / New
- $170,391
Hit the water in style and power with the 2025 Cobalt CS23 Surf, designed for ultimate performance, comfort, and versatility. Powered by a forward-facing Volvo V8-300CE-G DP engine... View Details

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$170,391
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2024 Mastercraft XT25

$173,240

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 25' / 9'
- 2024 / New
- $173,240
Contact us to find out ALL available savings! All Sale and/or Clearance Prices include all rebates and incentives. Introducing the all-new XT25. Completely redesigned from the hull... View Details

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$173,240
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2026 Barletta Lusso 25 UCA

$173,539

Antioch, IL
- Antioch, IL
- Pontoon
- 27' / 0'
- 2026 / New
- $173,539
Act fast on this limited-time offer! Elevate Your Escape Experience the ultimate water adventure with the 2026 Barletta LUSSO25UCA, a luxury pontoon that redefines relaxation and e... View Details

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$173,539
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2026 Robalo Cayman 266 SD

$174,855

Racine, WI
- Racine, WI
- Fishing Center Console
- 26' / 9'
- 2026 / New
- $174,855
Are you ready to take on the open waters in style? Look no further than this stunning 2026 Robalo Cayman 266 SD. With a sleek design and a variety of color options including Alloy... View Details

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$174,855
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2025 Mastercraft XT22

$176,058

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 9'
- 2025 / New
- $176,058
Contact us to find out ALL available savings! Versatility and flexibility are important when you want to please the crowd. The XT22 has you covered with seating for 16 and a spacio... View Details

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$176,058
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2025 Sea Ray SDX 270

$176,855

Antioch, IL
- Antioch, IL
- Runabout
- 27' / 0'
- 2025 / New
- $176,855
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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$176,855
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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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