Boats for sale in Chicago Illinois - BoatCrazy

1,579 boats found within 100 miles out of 15,725 Boats Found

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2025 Bayliner M17

$31,465

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 17' / 0'
- 2025 / New
- $31,465
Contact us to find out ALL available savings! This versatile, entry-level bowrider is great for couples and small families. It brings abundant storage, full windshield protection,... View Details

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$31,465
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2026 Harris CRUISER 210

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2026 / New
- Call for price
Just landed and ready to make waves! Introducing the 2026 Harris Cruiser 210, built without compromise. Invite your friends waterskiing, take the kids for a sun-soaked day of cruis... View Details

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2026 Harris CRUISER 230

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- Call for price
Act fast on this limited-time offer! Experience the Ultimate Adventure Introducing the stunning 2026 Harris 230CR, a masterpiece that embodies luxury and performance. Perfectly cra... View Details

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2022 Mastercraft NXT22

$89,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 2022 / Used
- $89,995
This 2022 NXT22 really well equipped with DockStar, Surfstar, advamced audio package, convertible rear seat, convenience package, removable ski pylon and tandom axle trailer. Intro... View Details

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$89,995
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2026 Harris CRUISER 210

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2026 / New
- Call for price
Every Special Edition Heritage Tritoon comes fully loaded with 150 HP, triple tubedstability, and premium blackout style. 2026 Harris 210CR: A New Dawn on the Water Experience the... View Details

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2026 Harris SOLSTICE 250

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 26' / 0'
- 2026 / New
- Call for price
Pursue adventure with the 2026 Harris Solistice 250. Reimagined and ready for action, the Solstice has more power, more luxury comfort and more standard features than ever before.... View Details

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2026 Harris CRUISER 230

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Harris Cruiser 230, built without compromise. Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a line.... View Details

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2026 Sea Ray SPX 210 Outboard

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Pewaukee, WI
- Pewaukee, WI
- Runabout
- 21' / 0'
- 2026 / New
- Call for price
Act fast on this limited-time offer! Experience Unmatched Performance Introducing the 2026 Sea Ray 21SPX-OB, where exhilarating performance meets effortless luxury. Tailored for ad... View Details

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2026 Harris CRUISER 190

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20' / 0'
- 2026 / New
- Call for price
Act fast on this limited-time offer! Experience Unmatched Elegance Introducing the 2026 Harris 190CR, a masterpiece of luxury and performance waiting to elevate your boating advent... View Details

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2025 Mastercraft NXT20

$110,275

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20' / 0'
- 2025 / New
- $110,275
Act fast on this limited-time offer! Explore the Waves in Style with the NXT20 Discover the perfect combination of affordability and excitement with the NXT20 boat. Measuring 20 fe... View Details

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$110,275
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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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2025 Harris 230 Cruiser

$69,615

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $69,615
Act fast on this limited-time offer! Experience Unmatched Adventure Introducing the 2025 Harris 230 Cruiser CWDH, where luxury meets performance on the water. Crafted for those who... View Details

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$69,615
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2025 Barletta LUSSO25UE

$141,296

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $141,296
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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$141,296
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2025 Barletta LUSSO25UC

$137,288

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $137,288
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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$137,288
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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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2025 Barletta ARIA20CC

$48,131

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20' / 0'
- 2025 / New
- $48,131
Contact us to find out ALL available savings! BARLETTA ARIA 20 CC Everything you love about the Barletta DNA with a price conscious approach. Is the Aria right for you? Designed to... View Details

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$48,131
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2025 Barletta LUSSO23UC

$137,834

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $137,834
Contact us to find out ALL available savings! BARLETTA LUSSO 23 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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$137,834
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2014 Tracker 175

$15,995

Leesburg, IN
- Leesburg, IN
- Fishing
- 17' / 7'
- 2014 / Used
- $15,995
NEW ARRIVAL!Come check out this awesome bass tracker that just came in for sale.Motor has been checked out and inspected by our service department.Put in water and go fishing! View Details

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$15,995
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2024 Starcraft LX 16 R

$26,995

Leesburg, IN
- Leesburg, IN
- Pontoon
- 17' / 8'
- 2024 / New
- $26,995
Kick back and enjoy summer sun with our LX series of versatile and affordable pontoons. Available in floorplans from 16' to 22', LX cruising models come with upgraded sea weave fl... View Details

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$26,995
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2025 Yamaha VF115XB

$12,874

Leesburg, IN
- Leesburg, IN
- Outboard Motors
- 0' / 0'
- 2025 / New
- $12,874
WE HAVE A NEW YAMAHA VF115XB AVAILABLE FOR REPOWER. Engine Type: In-Line Bore x Stroke: Bore: 3.19 in. (81 mm); Stroke: 3.5 in. (88.9 mm) Displacement: 111.8 cu. in. (1832 cc) Star... View Details

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$12,874
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1999 Monterey 236 BR

$14,895

Leesburg, IN
- Leesburg, IN
- Deck Boat
- 23' / 0'
- 1999 / Used
- $14,895
Mercruiser 7.4L 300 HP Bravo 3, TRL. View Details

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$14,895
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Showing 1534 to 1554 of 1,579 boats found.

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