Boats for sale in Chicago Illinois

1,199 boats found within 100 miles out of 14,810 Boats Found

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2026 Chaparral SSX 6

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Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 26' / 8'
- 2026 / New
- Call for price
Look no further-the SSX 6 is breaking barriers and setting the standard for on-water comfort and performance. Equipped with a state-of-the-art oversized touchscreen display, the he... View Details

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2026 Chaparral SSX 4

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Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 24' / 8'
- 2026 / New
- Call for price
The SSX 4 packs more elegance, performance, and innovation than boaters have ever experienced at this widely popular length. Its stylish lines, meticulous attention to detail, and... View Details

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2026 Chaparral 21 SSi

$73,189

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 21' / 8'
- 2026 / New
- $73,189
See this New 2026 Chaparral 21 SSi! How much fun can you pack into one summer? Plenty, aboard your new Chaparral. Trailerable to your favorite destinations. Nimble, efficient and p... View Details

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$73,189
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2026 Chaparral 21 SSi OB

$75,794

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 21' / 8'
- 2026 / New
- $75,794
Now on display, see this new 2026 Chaparral 21 SSi powered by a hearty 200 HP Yamaha 4-stroke outboard. Chaparral's innovative use of space means an abundance of cockpit space, sto... View Details

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$75,794
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2026 Chaparral 23 SSi

$89,259

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 23' / 8'
- 2026 / New
- $89,259
Everything that has made Chaparral's wildly popular SSi Series the talk of the waterways, gets bigger and better with the amazing 23 SSi. With a ChaparralONE price including the tr... View Details

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$89,259
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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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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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