Boats for sale in Chicago Illinois - BoatCrazy

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

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2019 Beneteau Oceanis 41.1

$289,000

Racine, WI
- Racine, WI
- Sailboat
- 40' / 13'
- 2019 / Used
- $289,000
2019 Beneteau Oceanis 41.1 This 2019 Beneteau Oceanis 41.1 is a rare opportunity to acquire a turnkey, revenue-producing sailboat with established demand, full utilization, and pr... View Details

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$289,000
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2026 Robalo Dual Console R317

$295,955

Racine, WI
- Racine, WI
- Performance
- 31' / 10'
- 2026 / New
- $295,955
Introducing the sleek and stylish 2026 Robalo Dual Console R317 - a true beauty on the water! This impressive boat is available in a stunning finish, reflecting the sun's rays in a... View Details

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$295,955
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2008 Trident 5012

$298,000

Chicago, IL
- Chicago, IL
- Commercial
- 50' / 0'
- 2008 / Used
- $298,000
Stock #481515 This Trident has been on the market for more than 30 days (Mar 9th). If you are thinking of making an offer, submit it today and let's make a deal! Excellent condit... View Details

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$298,000
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2026 Cobalt R8 Surf

$310,123

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27' / 8'
- 2026 / New
- $310,123
At its core is the upgraded Volvo V8-380CE forward-facing engine, delivering exhilarating performance with the smooth, confident handling Cobalt is known for. Whether you’re dialin... View Details

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$310,123
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2026 Cobalt R8 Surf

$321,502

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27' / 8'
- 2026 / New
- $321,502
Designed for those who expect flagship-level refinement, the R8 Surf immediately commands attention with its striking Slate and Ebony surf exterior, accented by satin black Cobalt... View Details

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$321,502
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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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2019 Formula 350 Crossover Bowrider

$325,000

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 35' / 10'
- 2019 / Used
- $325,000
See this Gorgeous fresh-water Formula 350 CBR with just 140 engine hours! Recent price reduction. Ready to go boating now. The 350 CBR offers an ideal combination of luxurious cock... View Details

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$325,000
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2003 Sea Ray 550 SUNDANCER

$334,995

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 55' / 0'
- 2003 / Used
- $334,995
2003 Sea Ray 550 Sundancer – Turn-Key Luxury with Extensive Upgrades This impeccably maintained 2003 Sea Ray 550 Sundancer combines proven performance, refined comfort, and timel... View Details

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$334,995
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2026 Cobalt R8 Surf

$338,985

Fontana, WI
- Fontana, WI
- Ski & Wake
- 27' / 8'
- 2026 / New
- $338,985
At the heart of this R8 Surf is the Volvo V8-430CE forward-facing engine, delivering next-level performance with deep reserves of torque and precision control. Whether you’re build... View Details

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$338,985
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2005 Sea Ray 500 Sundancer

$340,000

Holland, MI
- Holland, MI
- Yacht
- 50' / 0'
- 2005 / Used
- $340,000
02/22/2026 PRICE REDUCED TO $340,000| Motivated Seller Presenting this 2005 Sea Ray 500 Sundancer, a well-maintained freshwater express cruiser located on the Great Lakes and curr... View Details

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$340,000
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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 Mastercraft XSTAR

$354,977

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 23' / 0'
- 2025 / New
- $354,977
Act fast on this limited-time offer! Experience Unmatched Performance Introducing the 2025 Mastercraft XSTAR, where cutting-edge engineering meets exhilarating performance. This st... View Details

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$354,977
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2026 Robalo R317 Dual Console

$361,870

Racine, WI
- Racine, WI
- Performance
- 0' / 0'
- 2026 / New
- $361,870
On Order, Expected June 2026!! 2026 Robalo R317 Twin Yamaha F350USA2 4.3L V6 - White Hull - Yamaha Helm Master EX with Maneuverability - Cockpit Interior - Harbor Black - Canvas... View Details

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$361,870
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2024 Aviara AV32

$369,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Bowrider
- 32' / 10'
- 2024 / New
- $369,000
Contact us to find out ALL available savings! Aviara has redefined the modern day boat to bring you true luxury. This is the fusion of progressive design and effortless comfort, th... View Details

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$369,000
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2026 Dufour 37

$369,000

Racine, WI
- Racine, WI
- Sailboat
- 0' / 12'
- 2026 / New
- $369,000
2026 Dufour 37 This 2026 Dufour 37 is a rare opportunity to acquire a turnkey, revenue-producing sailboat with established demand, full utilization, and professional management al... View Details

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$369,000
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2026 Robalo Center Console R360

$515,435

Racine, WI
- Racine, WI
- Fishing Center Console
- 36' / 11'
- 2026 / New
- $515,435
Ahoy there, future sea captains and marine enthusiasts! Let's talk about this stunning 2026 Robalo Center Console R360 - the epitome of luxury and performance on the water. Picture... View Details

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$515,435
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2026 Cobalt R31

$527,175

Fontana, WI
- Fontana, WI
- Bowrider
- 31' / 9'
- 2026 / New
- $527,175
Frost Grey with a striking Knockout Red boot stripe & deep ebony hull, this R31 commands attention from every angle. Satin black COBALT lettering & sleek hull-side windows complete... View Details

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$527,175
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2026 Cobalt R31 Surf

$585,211

Fontana, WI
- Fontana, WI
- Ski & Wake
- 31' / 10'
- 2026 / New
- $585,211
This R31 Surf is equipped with twin Volvo 380hp forward-facing engines with joystick control, giving you effortless handling, pinpoint docking, and exhilarating acceleration at you... View Details

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$585,211
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2022 Cruisers 38 GLS

$604,900

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Cruiser
- 37' / 0'
- 2022 / Used
- $604,900
The ultimate family or entertainer's day boat! This stunning 2022 Cruisers Yachts 38 GLS is perfect for those who love to spend time on the water, offering luxurious amenities and... View Details

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$604,900
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2026 Cobalt R33

$606,461

Fontana, WI
- Fontana, WI
- Bowrider
- 33' / 10'
- 2026 / New
- $606,461
Powered by twin Volvo V8-380HP engines with joystick control, the R33 delivers smooth acceleration, confident handling, and effortless maneuverability in any conditions.Finished in... View Details

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$606,461
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2024 Dufour D470

$695,000

Racine, WI
- Racine, WI
- Sailboat
- 0' / 15'
- 2024 / New
- $695,000
2024 Dufour 470 | 3 Cabin Owner Version | Loaded | Available Now – No Wait If you’ve been researching new cruising sailboats in the 45–50 ft range, you already know: The biggest... View Details

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$695,000
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Showing 841 to 861 of 1,734 boats found.

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