Boats for sale in Chicago Illinois - BoatCrazy

1,568 boats found within 100 miles out of 15,515 Boats Found

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1984 Hatteras 60 CONTERTIBLE

$324,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Fishing Sportfish / Convertible
- 60' / 0'
- 1984 / Used
- $324,900
A Flagship Hatteras with a rich history, and way too many upgrades to list. The 2nd owner bought the boat in 1988, and brought it to Southern Wisconsin. It was pampered and service... View Details

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$324,900
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2026 Sea Ray Sundancer 370

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 38' / 0'
- 2026 / New
- Call for price
Step into luxury with the Sea Ray Sundancer 370: Indulge in the ultimate on-water experience aboard the Sea Ray Sundancer 370. This magnificent boat offers a perfect blend of luxur... View Details

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2026 Cruisers 42 GLS

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 42' / 0'
- 2026 / New
- Call for price
Navigate waters with ease in the 2026 Crusiers Yachts 42 GLS. Powered by Mercury engines reach speeds up to 48 mph. With dual beach doors, a full galley, comfortable seating, and s... View Details

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2026 Cruisers 42 GLS Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 44' / 0'
- 2026 / New
- Call for price
If adventure is your main goal when it comes to boating, look no further than the fast, stylish, and fun 42 GLS Outboard. With dual beach doors, a U-shaped dinette, galley with a r... View Details

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2026 Sea Ray Sundancer 370 Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 40' / 0'
- 2026 / New
- Call for price
Introducing the 2025 Sea Ray Sundancer 370 Outboard Experience the perfect blend of luxury and performance with the 2026 Sea Ray Sundancer 370 Outboard. This stunning cruiser boast... View Details

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2026 Cruisers 42 Cantius

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 43' / 0'
- 2026 / New
- Call for price
Handcrafted American legacy. With a rich history and unrivaled passion, Cruisers Yachts creates American-made boats for the world. With 360 degree windows and an open-plan main dec... View Details

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2002 Crownline 215 CCR

$15,495

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cuddy Cabin
- 22' / 0'
- 2002 / Used
- $15,495
2002 Crownline 215 CCR View Details

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$15,495
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2005 Regal COMMODORE 4260

$199,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 45' / 0'
- 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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2008 Regal 2860 WINDOW EXPRESS

$49,995

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 29' / 0'
- 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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2026 Azimut 48 Verve

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Yacht
- 48' / 0'
- 2026 / New
- Call for price
Seize this exclusive opportunity! The Azimut Yachts 48 Verve is a bold expression of Italian performance and luxury, redefining what a modern sport cruiser can be. Designed for own... View Details

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2026 Tiara 48LE

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 48' / 0'
- 2026 / New
- Call for price
Seize this exclusive opportunity! 2025 Tiara Yachts 48 LE Step aboard the 2025 Tiara Yachts 48 LE, where luxury meets performance. This stunning vessel features three powerful Merc... View Details

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2026 Cruisers 34 GLS Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 36' / 0'
- 2026 / New
- Call for price
The 2026 Cruisers Yachts 34 GLS Outboard for sale near you offers all of the excitement of the 34 GLS I/O with the unsurpassed ease of maintenance of outboard engines. THe 34 GLS'... View Details

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2011 Cobalt 296

$84,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 30' / 0'
- 2011 / Used
- $84,900
What an absolute creampuff!! This indoor-kept/rack-stored (summer & winter) fresh water 2011 Cobalt 296 is the discerning shopper's dream. The pictures do not deceive; in fact... View Details

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$84,900
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2026 Cruisers 38 GLS

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 37' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Cruisers Yachts 38 GLS. With a drop-down beach door, hydraulic swim platform, and spacious bow lounge, the 38 GLS I/O for sale near you brings your day boating... View Details

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2026 Cruisers 38 GLS Outboard

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 38' / 0'
- 2026 / New
- Call for price
The 2026 Cruisers Yachts 38 GLS Outboard combines the unmatched performance and entertainment capabilities of the 38 GLS with powerful, easy-to-maintain outboards. Expand your swim... View Details

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2026 Cruisers 34 GLS

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 37' / 0'
- 2026 / New
- Call for price
The 2026 Cruisers Yachts 34 GLS inboard includes open bow seating, a spacious cockpit with galley, and joystick piloting allowing you to navigate at speeds up to 47 mph. Feel the p... View Details

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2026 Cruisers 50 Cantius

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 49' / 0'
- 2026 / New
- Call for price
Seize this exclusive opportunity! The 2026 Cruisers Yachts 50 Cantius represents the perfect balance of luxury, performance, and innovative design—continuing a legacy built on deca... View Details

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2026 Saxdor 320 GTC

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 32' / 0'
- 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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2025 Sea Ray SLX 310

$349,152

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Bowrider
- 31' / 0'
- 2025 / New
- $349,152
Contact us to find out ALL available savings! The SLX 310 demands everyone's full attention. And by everyone we mean not only the abundance of people who can lounge comfortably onb... View Details

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$349,152
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2025 Bayliner Element E18

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 18' / 0'
- 2025 / New
- Call for price
2025 Bayliner Element E18 Experience the ultimate aquatic adventure with the stunning 2025 Bayliner Element E18. This luxury vessel combines exceptional performance with exquisite... View Details

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2025 Aviara AV28S

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Winthrop Harbor, IL
- Winthrop Harbor, IL
- Runabout
- 0' / 0'
- 2025 / New
- Call for price
Experience Luxury on the Water with the 2025 Aviara AV28S Step aboard the Aviara AV28S and elevate your boating adventures to new levels of luxury and performance. Crafted with pre... View Details

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Showing 22 to 42 of 1,568 boats found.

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