Boats for sale in Chicago Illinois

1,677 boats found within 100 miles out of 15,116 Boats Found

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2026 Walker Bay 22

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Racine, WI
- Racine, WI
- Performance
- 0' / 0'
- 2026 / New
- Call for price
The Walker Bay 22. The Walker Bay 22 is a luxury runabout boat designed with a wide beam, giving both the driver and passengers plenty of space and comfort—something you’d typicall... View Details

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2026 Walker Bay G12

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Racine, WI
- Racine, WI
- Performance
- 0' / 0'
- 2026 / New
- Call for price
The Generation 12 - The World’s Best 12’ Outboard Console Tender Generation 12 Features and Specifications Specifications: LOA – 365cm / 12’ Beam – 134cm / 6’ 4” Tube Diameter – 48... View Details

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2026 Walker Bay G15

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Racine, WI
- Racine, WI
- Performance
- 0' / 0'
- 2026 / New
- Call for price
2026 Walker Bay G15 Introducing the all-new Generation 15 luxury outboard console tender. The G15 is quite possibly the most sophisticated and exciting RIB we’ve ever made. Over 25... View Details

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2026 Gala V330

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Racine, WI
- Racine, WI
- Performance
- 10' / 5'
- 2026 / New
- Call for price
GALA Viking V330 Mercury ME 30 ELPT Ez Loader Galvanized Trailer V330 Boat Specs: - LOA: 10'10" - Beam: 5'8" - Bare Boat Weight: 297 lbs - Loading Capacity: 1100 lbs / 5 Person... View Details

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2026 Gala V360

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Racine, WI
- Racine, WI
- Performance
- 11' / 6'
- 2026 / New
- Call for price
2026 GALA - V360 Honda BF40LRTA 40hp. Four Stroke Outboard Engine EZ Loader Galvanized Trailer GALA Factory options included on this V360: - Electric package: horn, navigation... View Details

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2026 Gala Galaxy P8

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Racine, WI
- Racine, WI
- Performance
- 0' / 0'
- 2026 / New
- Call for price
GALAXY – Pilot P8 model is one of our most popular and best selling models for professional use. Main application for this boat are: • A number of commercial applications like WHA... View Details

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2026 Gala V420

$33,429

Racine, WI
- Racine, WI
- Performance
- 13' / 6'
- 2026 / New
- $33,429
Manufacturer images utilized, In Stock unit equipped with gray eva non-skid. 2026 Gala V420 Honda BF60LRT Trailmaster CR1515 trailer The VIKING V420, this mid-size luxury al... View Details

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$33,429
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1987 Hunter Legend 37

$35,000

Racine, WI
- Racine, WI
- Sailboat
- 37' / 12'
- 1987 / Used
- $35,000
1987 Hunter Legend 37 Large main salon with dinnett to port and settee to starboard, nav station to starboard, full galley with 2 burner stove / oven, double stainless sink and re... View Details

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$35,000
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1989 Hunter 30

$22,000

Racine, WI
- Racine, WI
- Sailboat
- 30' / 11'
- 1989 / Used
- $22,000
1989 Hunter 30 "Silent Knight" This is a very nice freshwater boat, very well maintained for an 89'. - Starting aft, this boat offers the swim platform with stainless steel swim... View Details

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$22,000
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1996 Caliber 1 35 LRC

$85,000

Racine, WI
- Racine, WI
- Sailboat
- 35' / 11'
- 1996 / Used
- $85,000
1996 Caliber 35 LRC "Archangel" This is a single owner vessel, purchased new in '96 and used exclusivley for cruising Lake Michigan. The boat has been really well cared for as wa... View Details

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$85,000
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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 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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2001 Regal 1900 LSR

$9,000

Racine, WI
- Racine, WI
- Performance
- 18' / 8'
- 2001 / Used
- $9,000
New Listing! Vessel Available! 2001 Regal 1900 LSR Powered by the Volvo Penta 4.3 GL Bimini Top Cockpit and bow storage cover Single axle trailer Misc. life jackets included... View Details

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$9,000
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2007 Hunter 38

$109,000

Racine, WI
- Racine, WI
- Sailboat
- 0' / 12'
- 2007 / Used
- $109,000
2007 Hunter 38 Available for viewing!! Overview If you’ve been waiting for the right cruising sailboat—this is it. This 2007 Hunter 38 delivers the perfect combination of perfo... View Details

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$109,000
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2004 Chaparral 280 SSi

$44,000

Waterford, WI
- Waterford, WI
- Bowrider
- 28' / 0'
- 2004 / Used
- $44,000
Stock #487201 Reason for selling is "Buying a smaller boat". This is a new advertisement, on the market just this week (Apr 20th). Always accepting offers! Large bowrider with t... View Details

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$44,000
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2019 Supra SA400

$115,000

Delavan, WI
- Delavan, WI
- Ski & Wake
- 25' / 0'
- 2019 / Used
- $115,000
Stock #360586 Reason for selling is "Plans changed". ANY and ALL offers will be put in front of our seller! Submit your offer today! 350HP INDMAR! TRAILER INCLUDED!! READY TO PL... View Details

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$115,000
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2016 Chaparral 290 Signature

$138,900

South Bend, IN
- South Bend, IN
- Cruiser
- 29' / 9'
- 2016 / Used
- $138,900
Stored Off Site, Shown By Appointment ONLY please! Most cruisers in this size range require you to wake up and disassemble the forward berth if you want to use the dinette for an... View Details

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$138,900
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1999 Sea Ray 500 Sundancer

$199,000

South Haven, MI
- South Haven, MI
- Express Cruiser
- 50' / 0'
- 1999 / Used
- $199,000
Stock #471094 Video of this vessel available at www [dot] popsells [dot] com/view/471094 Reason for selling is "Has not used enough". ANY and ALL offers will be put in front of... View Details

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$199,000
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2023 Custom Built 25 Hadlee Houseboat

$69,000

South Haven, MI
- South Haven, MI
- Houseboat
- 25' / 8'
- 2023 / Used
- $69,000
Custom Built Houseboat Immerse yourself in stylish and comfortable houseboat living with this newly built 2023 Hadley Houseboat, only the third one built, the other two have b... View Details

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$69,000
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2021 Sylvan L3 LZ

$38,700

Edwardsburg, MI
- Edwardsburg, MI
- Pontoon
- 24' / 0'
- 2021 / Used
- $38,700
Stock #452780 Video of this vessel available at www [dot] popsells [dot] com/view/452780 Reason for selling is "Doesn't use it. Came with the home.". ANY and ALL offers will be... View Details

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$38,700
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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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