Boats for sale in Chicago Illinois - BoatCrazy

1,733 boats found within 100 miles from Chicago, Illinois

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2025 Yamaha 195S

$48,519

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19' / 0'
- 2025 / New
- $48,519
Contact us to find out ALL available savings! MSRP: $54,287 Sale Price: $54,737 All Sale and/or Clearance Prices include all rebates and incentives. View Details

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$48,519
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2025 Harris 210 Cruiser

$46,014

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $46,014
Contact us to find out ALL available savings! HARRIS 210 CRUISERS SLDH Invite your friends waterskiing, take the kids for a sun-soaked day of cruising, or escape alone and cast a l... View Details

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$46,014
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2025 Bayliner VR4OB

$39,241

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 18' / 0'
- 2025 / New
- $39,241
Contact us to find out ALL available savings! Act fast on this limited-time offer! The latest in our VR Series of highly evolved bowriders the VR4 is easy to tow launch and store a... View Details

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$39,241
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2025 Yamaha AR220

$56,022

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 22' / 0'
- 2025 / New
- $56,022
Contact us to find out ALL available savings! Sale Price: $62,387 All Sale and/or Clearance Prices include all rebates and incentives. View Details

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$56,022
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2025 Bayliner VR4OB

$38,614

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 18' / 0'
- 2025 / New
- $38,614
Contact us to find out ALL available savings! Act fast on this limited-time offer! The latest in our VR Series of highly evolved bowriders the VR4 is easy to tow launch and store a... View Details

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$38,614
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2026 Harris CRUISER 190

$41,727

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20' / 0'
- 2026 / New
- $41,727
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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$41,727
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2025 Bayliner VR4

$41,946

Pewaukee, WI
- Pewaukee, WI
- Bowrider
- 18' / 0'
- 2025 / New
- $41,946
Contact us to find out ALL available savings! Act fast on this limited-time offer! The latest in our VR Series of highly evolved bowriders the VR4 is easy to tow launch and store a... View Details

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$41,946
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2025 Barletta ARIA20CC

$50,001

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20' / 0'
- 2025 / New
- $50,001
Contact us to find out ALL available savings! Everything you love about the Barletta DNA with a price conscious approach. Is the Aria right for you? Designed to be obtainable witho... View Details

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$50,001
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2025 Sea Ray SPX 210

$83,889

Pewaukee, WI
- Pewaukee, WI
- Runabout
- 21' / 0'
- 2025 / New
- $83,889
Act fast on this limited-time offer! Discover the Sea Ray SPX 210 Embark on thrilling aquatic adventures with the Sea Ray SPX 210, a vessel designed for pure excitement and unforge... View Details

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$83,889
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2025 Yamaha 252S

$84,760

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 25' / 0'
- 2025 / New
- $84,760
Contact us to find out ALL available savings! EXCELLENCE HAS ARRIVED With Yamaha E-Series features, the 252SE sets a new bar for modern style, technology, and convenience. View Details

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$84,760
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2023 Mastercraft X22

$159,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22' / 0'
- 2023 / New
- $159,995
Contact us to find out ALL available savings! All Sale and/or Clearance Prices include all rebates and incentives. Now is the time and luxury performance is the mission. The X22 br... View Details

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$159,995
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2026 Sylvan L-3 CLZ DH

Call for price

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 24' / 0'
- 2026 / New
- Call for price
Act fast on this limited-time offer! Experience Unmatched Luxury Introducing the exquisite 2026 Sylvan L-3 CLZ DH, a masterpiece of craftsmanship and design, located at SkipperBud'... View Details

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2026 Starcraft SVX 211 OB

Call for price

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 20' / 0'
- 2026 / New
- Call for price
Act fast on this limited-time offer! Elevate Your Escape with the 2026 Starcraft 210SVXDCOB Discover the ultimate freedom on the waves with the 2026 Starcraft 210SVXDCOB, available... View Details

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2025 Starcraft RX 23 DL DHTT

$105,078

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $105,078
Contact us to find out ALL available savings! Act fast on this limited-time offer! The CX pontoon boat series is everything you'd expect from Starcraft. With countless layouts and... View Details

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$105,078
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2026 Starcraft 211SVXIO

$66,820

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 21' / 0'
- 2026 / New
- $66,820
Act fast on this limited-time offer! Experience Luxury on the Water Step aboard the stunning 2026 Starcraft 211SVXIO and immerse yourself in a world of elegance and adventure. This... View Details

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$66,820
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2025 Starcraft RX 23 Q DH TT

$106,416

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $106,416
Contact us to find out ALL available savings! Act fast on this limited-time offer! The CX pontoon boat series is everything you'd expect from Starcraft. With countless layouts and... View Details

View 20 Photos and Details Contact Seller

$106,416
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2026 Starcraft EXS 3 DL

Call for price

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2026 / New
- Call for price
Act fast on this limited-time offer! The Starcraft EXS 3 DL is a feature-rich pontoon boat with dual rear-facing loungers and a spacious layout designed for cruising and fun on the... View Details

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2025 Starcraft EXS 3 Q TT

$60,364

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $60,364
Contact us to find out ALL available savings! Act fast on this limited-time offer! 2025 Starcraft 3EXSQ: The Pinnacle of Luxury on Water Introducing the 2025 Starcraft 3EXSQ, a ves... View Details

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$60,364
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2026 Starcraft SVX 191 OB

$55,742

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 18' / 0'
- 2026 / New
- $55,742
Act fast on this limited-time offer! Starcraft's SVX 191 OB fiberglass sport boat is tailored for family adventures, offering a thrilling combination of speed and comfort on the wa... View Details

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$55,742
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2026 Starcraft EXS 3 Q DH

$61,722

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2026 / New
- $61,722
Act fast on this limited-time offer! Experience Luxury on the Water Introducing the 2026 Starcraft EXS3QDH, a masterpiece designed for those who seek adventure and elegance on the... View Details

View 6 Photos and Details Contact Seller

$61,722
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2026 Starcraft SVX 191 OB

$53,173

Pewaukee, WI
- Pewaukee, WI
- Deck Boat
- 18' / 0'
- 2026 / New
- $53,173
Just landed and ready to make waves! Act fast on this limited-time offer! Starcraft's SVX 191 OB fiberglass sport boat is tailored for family adventures, offering a thrilling combi... View Details

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$53,173
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Showing 1513 to 1533 of 1,733 boats found.

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