Boats for sale in Chicago Illinois

1,171 boats found within 100 miles out of 14,815 Boats Found

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2000 Crownline 290 CR

$34,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 31' / 10'
- 2000 / Used
- $34,900
This Crownline 290 CR is a spacious small express cruiser powered by twin Mercruiser 5.7 EFI's and NEW Bravo III drives! She has about 700 hours on her hour meters and appears to h... View Details

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$34,900
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2021 Qwest LS 822 DS Bar

$49,900

Saint Joseph, MI
- Saint Joseph, MI
- Pontoon
- 22' / 8'
- 2021 / Used
- $49,900
This 2021 Qwest LS 822 perfectly blends style and performance with great fishing capabilites. Power by a 200HP Honda and Upgraded tiple toon package and aluminum underskining makes... View Details

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$49,900
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2017 Chaparral 330 Signature

$194,900

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 33' / 10'
- 2017 / Used
- $194,900
Now available, see this 2017 Chaparral 330 Signature. Always fresh-water, with just 243 engine hours. Designed for summer adventures and weekend getaways, the Chaparral 330 Signatu... View Details

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$194,900
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2018 Chaparral 191 Suncoast

$37,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 20' / 8'
- 2018 / Used
- $37,900
The 191 Suncoast breaks down boating to its basics, while not sacrificing the Chaparral design, style, and quality you have come to expect. A large open concept seating arrangement... View Details

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$37,900
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2016 Chaparral 307 SSX

$134,900

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 30' / 9'
- 2016 / Used
- $134,900
Meet your next on-the-water obsession: the 2016 Chaparral 307 SSX a head turning mix of luxury, performance, and pure boating bliss! At 30 feet, she delivers a ride as smooth as s... View Details

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$134,900
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2000 Chaparral Signature 300

$37,500

Saint Joseph, MI
- Saint Joseph, MI
- Cruiser
- 29' / 10'
- 2000 / Used
- $37,500
If you are looking for a small family cruiser with all the amenities you just found it! This Chaparral Signature 300 has all the creature comforts including Air Conditioning, Fusio... View Details

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$37,500
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1977 Trojan F30 Express

$10,900

Saint Joseph, MI
- Saint Joseph, MI
- Express Cruiser
- 30' / 11'
- 1977 / Used
- $10,900
NEW PRICE!! MAKE OFFER!! This classically-styled Trojan Hardtop is sure to turn heads in every harbor. With a fully sheltered helm and canvassed aft deck, there's plenty of room f... View Details

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$10,900
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2024 Aquador 250 HT

$266,256

Racine, WI
- Racine, WI
- Cruiser
- 25' / 8'
- 2024 / New
- $266,256
2024 Aquador 250 HTSuzuki DF250APOptional Factory Equipment Included:Air Conditioning unit DC inverterAnchor winch, bow + anchor 7.5kg + remote control for bow thruster and winchAn... View Details

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$266,256
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1983 Marlow Hunter 27 Cherubini

$15,500

Racine, WI
- Racine, WI
- Sailboat
- 27' / 9'
- 1983 / Used
- $15,500
This 1983 Hunter 27 (Tall Rig) has been cared for and loved for many years. The boat has been maintained to a very high level, which will leave a lucky new owner with less headache... View Details

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$15,500
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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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