Boats for sale in Chicago Illinois - BoatCrazy

883 boats found within 100 miles from Chicago, Illinois

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2026 Azimut Verve 42

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 42'
- 2026 / New
- Call for price
Rebellious energy and excitement come to life in the Verve 42. Forward-facing and adrenalinic, this performance-driven outboard yacht incorporates a fast and compact nature, while... View Details

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2018 Crownline 264 CR

$68,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 26'
- 2018 / Used
- $68,000
Trailer Included! Priced to sell! Great opprotunity! Powered by a MerCruiser 6.2L MPI 300 HP V8 with a Bravo III dual-prop drive, the 264 CR delivers smooth handling, strong perfor... View Details

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$68,000
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2026 Sea Ray SDX 250

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 25'
- 2026 / New
- Call for price
Elegant design. Superior performance. The 2026 Sea Ray SDX is engineered to offer exceptional capability for full days spend on the water. This adaptable sterndrive model features... View Details

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1999 Silverton 322AFTCABIN

$49,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 32'
- 1999 / Used
- $49,900
Great opportunity to own a fresh water, 32' Silverton aft cabin. 460 hours on upgraded 454 EFI Crusaders. Newer canvas and radar/plotter, and fantastic staterooms, and salon/galley... View Details

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$49,900
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2026 Saxdor 340 GTWA

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Performance
- 34'
- 2026 / New
- Call for price
Just landed and ready to make waves! The Saxdor 340 GTWA is designed to offer both accessibility and comfort, creating an expansive space perfect for leisure activities and providi... View Details

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1996 Sea Ray 290 SUNDANCER

$34,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 29'
- 1996 / Used
- $34,900
Ready for viewing, , Upgraded, Cleaned, 680 Engine Hours, Turn Key!!! Experience timeless styling, impressive performance, and exceptional care with this 1996 Sea Ray 290 Sundancer... View Details

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$34,900
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2000 Sea Ray 460 SUNDANCER

$209,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 46'
- 2000 / Used
- $209,900
2000 Sea Ray 460 SUNDANCER View Details

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$209,900
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2026 Saxdor 320 GTC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 32'
- 2026 / New
- Call for price
Act fast on this limited-time offer! Experience Ultimate Luxury with the 2025 Saxdor 320 GTC! Introducing the breathtaking 2025 Saxdor 320 GTC, where impeccable design meets exhila... View Details

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2026 Sea Ray SDX 290

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 29'
- 2026 / New
- Call for price
Built for fun, introducing the 2026 Sea Ray SDX 290. When an active family loves water sports, they generall want to share their good times with friends. That's where the SDX 290 c... View Details

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2008 Regal 2860 WINDOW EXPRESS

$49,995

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 29'
- 2008 / Used
- $49,995
Loved by its only owners since new, this exclusively fresh water and locally serviced Regal is awaiting a new home. She boasts a ton of space for her size with the ability to sleep... View Details

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$49,995
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2005 Regal COMMODORE 4260

$199,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 45'
- 2005 / Used
- $199,900
Regal's beloved 4260 Commodore! The lay out was one of Regal's best, and package with this boat with rebuilt Yanmars with less than 250 hours since rebuild, it will be perfect for... View Details

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$199,900
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2026 Sea Ray Sundancer 320 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 32'
- 2026 / New
- Call for price
The value of a cruiser and a sport-combined. Introducing the 2026 Sea Ray Sundancer 320 Outboard. Combining the values of a cruiser and a sport-boat/bowrider in a brilliant package... View Details

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2026 Scout 305 LXF

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 30'
- 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 240 XSF

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 24'
- 2026 / New
- Call for price
Sleek lines, innovation and high performance make this 240 XSF the hottest boat in its class. Built on Scout's revolutionary NuV3 fuel efficient hull design, this forward seating c... View Details

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2026 Scout 281 XSS

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 28'
- 2026 / New
- Call for price
Introducing Scout's newest flagship Bay Boat model, the 281 XSS. They sesigned this model to be like no other bay boat or inshore/offshore crossover on the market, thanks to its ad... View Details

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2026 Scout 215 XSF

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 22'
- 2026 / New
- Call for price
The 215 XSF is built on Scout's revolutionary fuel saving NuV3 hull design, while the deck offers ample standard amenities for everything from serious fishing to comfort cruising.... View Details

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2026 Scout 195 Sportfish

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 19'
- 2026 / New
- Call for price
This 19-footer measures 19'5" in length with a wide beam of 8'6" offering vast space to not only move around freely onboard but to also land the big catch of the day. Standard swim... View Details

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2026 Scout 260 LXF

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 26'
- 2026 / New
- Call for price
Introducing our all-new 260 LXF center console model. Performance meets function at a high level in this new 26' model. It comes standard with an integrated exposed carbon fiber T-... View Details

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2026 Scout 175 Sportfish

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 17'
- 2026 / New
- Call for price
Take home a piece of engineering genius: the 2026 Scout 175 Sportfish. This stylishly-polished model delivers a vast array of fishing features, including a 94-quart removable coole... View Details

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2026 Scout 188 Sportfish

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Center Console
- 19'
- 2026 / New
- Call for price
From the company that has brough many firsts to the coastal fishin boat segment, they introduce their new 188 Sportfish. This model sets a new bar by incorporating many features no... View Details

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2026 Scout 175 Sport Dorado

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 17'
- 2026 / New
- Call for price
Whether the day calls for a run out to your favorite fishing spot, tubing with the kids or just an evening cruise through the back country, the 175 Sport Dorado is up for the adven... View Details

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Showing 22 to 42 of 883 boats found.

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