Boats for sale in Chicago Illinois

1,200 boats found within 100 miles out of 14,788 Boats Found

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2025 Robalo R160 Center Console

$41,430

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 16' / 7'
- 2025 / New
- $41,430
The R160 makes every on-water adventure more fun in a size that's easy to trailer and store. But don't think that it isn't designed with performance in-mind. Featuring the same on-... View Details

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$41,430
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2025 Chaparral 307 SSX

Call for price

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30' / 9'
- 2025 / New
- Call for price
Now in stock! Step aboard one of Chaparral's most innovative designs - the spacious, sleek and powerful 307 SSX. With an abundance of comfortably contoured cockpit seating, lot of... View Details

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2004 Bayliner 245

$23,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 24' / 8'
- 2004 / Used
- $23,900
Bayliner's 245 Cruiser sports a comfortable cockpit and convenient cabin arrangement. The cockpit area includes a reversible portside companion seat -- converting from a forward fa... View Details

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$23,900
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2006 Chaparral 310 Signature

$69,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 31' / 10'
- 2006 / Used
- $69,900
This 2006 Chaparral 310 Signature is a sleek and luxurious cruiser designed for thosewho appreciate both performance and comfort on the water. With a length overall of 33 feet and... View Details

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$69,900
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1995 Sea Ray 400 Express Cruiser

$62,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 40' / 13'
- 1995 / Used
- $62,900
Nicely maintained fresh-water Sea Ray 400 Express. Twin Merc 454's with 537 engine hours, original. This classic express cruiser helped usher in the new era mid-'90's Sea Ray desig... View Details

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$62,900
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1977 Martin Trauf Trawler 40

$45,000

Saint Joseph, MI
- Saint Joseph, MI
- Commercial
- 40' / 0'
- 1977 / Used
- $45,000
Stock #445784 Reason for selling is "Not Using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Working Steel-Hull Commercial Dive Boat, Strong... View Details

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$45,000
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1997 Bayliner 2655 Ciera

$19,900

Harvard, IL
- Harvard, IL
- Express Cruiser
- 26' / 0'
- 1997 / Used
- $19,900
Stock #365912 Video of this vessel available at www [dot] popsells [dot] com/view/365912 ANY and ALL offers will be put in front of our seller! Submit your offer today! FRESH WA... View Details

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$19,900
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2023 Gala V330

$18,999

Racine, WI
- Racine, WI
- Inflatable
- 10' / 5'
- 2023 / New
- $18,999
2023 GALA Viking V330Honda BF30D3LRTTrailmaster CR1515V330 Boat Specs:• LOA: 10'10"• Beam: 5'8"• Bare Boat Weight: 275 lbs• Loading Capacity: 1100 lbs / 5 Persons• Engine Max: 30 H... View Details

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$18,999
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2023 Robalo R-266 Deepwater Black Wide Band

$149,900

Racine, WI
- Racine, WI
- Fishing Center Console
- 26' / 9'
- 2023 / Used
- $149,900
2023 Robalo 266 Cayman - Deepwater BlackMercury Verado DTS 400XXLCoyote Tandem Axle Aluminum Trailer266 Cayman Unique Key Features:• 2 Passenger Flip-up Transom w/ High Backrest• 3... View Details

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$149,900
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2025 Robalo Center Console R250

$193,625

Racine, WI
- Racine, WI
- Fishing Center Console
- 25' / 9'
- 2025 / New
- $193,625
2025 Robalo R250 - In Stock!Twin Mercury DTS 200XLCoyote Aluminum Tandem Axle TrailerStandard Factory Options Included With this Package:• Solid Hull Alloy Gray Gel Coat• Cockpit I... View Details

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$193,625
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1986 Krogen 38 Cutter

$60,000

Racine, WI
- Racine, WI
- Sailboat
- 44' / 12'
- 1986 / Used
- $60,000
1986 Krogen Cutter 38"Intrepid"Intrepid has had two owners and has resided on the freshwater of Lake Michigan since 2012. Designed by James S. Krogen and built by Kady-Krogen Yacht... View Details

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$60,000
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2024 Dufour D470

$695,000

Racine, WI
- Racine, WI
- Sailboat
- 48' / 15'
- 2024 / New
- $695,000
2024 DuFour 470• 3 cabins 2 heads, toilets equipped with holding tanks• Infused hull• LED interior lights + indirect light• Upgrade to 75 hp engine - Saildrive• 4 blades folding pr... View Details

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$695,000
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2000 Hunter 410

$116,000

Racine, WI
- Racine, WI
- Sailboat
- 43' / 13'
- 2000 / Used
- $116,000
2000 Hunter 410 - "Cabaret"This Hunter has been maintained very well over its life, kept on the Great Lake Michigan. Take your family sailing in comfort and let your worries sail a... View Details

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$116,000
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1994 Pacific Seacraft 34

$110,000

Racine, WI
- Racine, WI
- Sailboat
- 34' / 10'
- 1994 / Used
- $110,000
1994 Pacific Seacraft 34"Esmerelda"This William Crealock designed 1994 Pacific Seacraft cutter is ready for your next sailing adventure. The vessel has been stored indoors througho... View Details

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$110,000
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2023 Robalo R-222 White

$84,500

Racine, WI
- Racine, WI
- Fishing Center Console
- 21' / 8'
- 2023 / New
- $84,500
2023 ROBALO R222 - WhiteYamaha Four Stroke F200XB 200H.PCoyote Aluminum Tandem Axle trailerSPECS:LOA: 21' 6"Beam: 8' 6"Bridge Clearance with Hardtop: 8' 7"Deadrise: 21°Fuel Capacit... View Details

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$84,500
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2025 Grand G500HLF

$65,000

Racine, WI
- Racine, WI
- Inflatable
- 16' / 7'
- 2025 / New
- $65,000
Boat is on site, Inquire for more Info!2025 Grand Marine G500HLFHonda BF115EZ Loader TrailerOptional Equipment Included with this model• Artic Grey Hypalon tube• Seadek grey/black,... View Details

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$65,000
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1983 O Day 34

$35,000

Racine, WI
- Racine, WI
- Sailboat
- 34' / 11'
- 1983 / Used
- $35,000
1983 O'Day 34"Dawn Treader"The O'Day 34. This boat offers plenty of comfortable room below deck and a spacious cockpit which make this a great weekend cruiser and daysailer! Winter... View Details

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$35,000
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2019 Beneteau Oceanis 35.1

$164,699

Racine, WI
- Racine, WI
- Sailboat
- 34' / 12'
- 2019 / Used
- $164,699
2019 Beneteau Oceanis 35.1GENERAL SPECIFICATIONSOverall Length (L.O.A): (without bowsprit): 34’3’’Hull length: 32’9’’L.W.L.: 31’10’’Hull Beam: 12’2’’Light displacement: 13,149 lbsS... View Details

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$164,699
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1987 Bayfield 32C

$30,000

Racine, WI
- Racine, WI
- Sailboat
- 32' / 10'
- 1987 / Used
- $30,000
1987 Bayfield 32CEmbark on your next adventure with this beautifully crafted Bayfield Yachts cutter rig, a timeless vessel built in Ontario, Canada. Designed for durability and per... View Details

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$30,000
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2023 Gala V330

$17,999

Racine, WI
- Racine, WI
- Inflatable
- 10' / 0'
- 2023 / New
- $17,999
2023 GALA Viking V3302023 Mercury ME 30 ELPTTrailmaster CR1515V330 Boat Specs:• LOA: 10'10"• Beam: 5'8"• Bare Boat Weight: 275 lbs• Loading Capacity: 1100 lbs / 5 Persons• Engine M... View Details

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$17,999
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2025 Robalo Center Console R230

$120,549

Racine, WI
- Racine, WI
- Fishing Center Console
- 23' / 8'
- 2025 / New
- $120,549
2025 Robalo R230 - Solid WhiteMercury 250XLCoyote Aluminum Tandem Axle TrailerFactory Options Included With this Package:• White Hull• Cockpit Interior - Harbor Black• Canvas Color... View Details

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$120,549
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