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Boats for sale in Chicago Illinois

There are 1208 new and used boats for sale in Chicago, Illinois. Browse Cruiser, Runabout, Pontoon, Fishing, Ski & Wake, and Center Console from brands like Sea Ray, Scout, Harris, Mastercraft, Cruisers, and Bayliner on BoatCrazy. View a wide selection of boats from $300 to $3,395,000.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
1,208 boats found within 100 miles out of 14,706 Boats Found
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  • Price Drop 1994 Rinker 190 CAPTIVA (175 HP MCM)

    1994 Rinker 190 CAPTIVA (175 HP MCM)

    $1,496
    La Porte, IN
    • La Porte, IN
    • Cruiser
    • 19' / 8'
    • 1994 / Used
    • $1,496

    ️ 1994 Rinker 190 Captiva – Affordable Bowrider Opportunity Turn heads on the water with this classic 19-foot Rinker Captiva—an ideal platform for restoration or repower. With its... View Details

    View 12 Photos and Details Contact Seller
    $1,496
    VIEW DETAILS
  • 2018 Coach 230C

    2018 Coach 230C

    $34,900
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 24' / 8'
    • 2018 / Used
    • $34,900

    The Coach Cruise series is based on a timeless classic in the pontoon industry, only Coach brought it up a notch. With suspension foam seats, soft touch vinyl, standard chaise loun... View Details

    View 21 Photos and Details Contact Seller
    $34,900
    VIEW DETAILS
  • 2026 Viaggio LAGO V20S TRITOON

    2026 Viaggio LAGO V20S TRITOON

    $51,052
    La Porte, IN

    New 2026 Viaggio Lago V20S TRITOON with BF 140 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. Upgrades Include: Tube Protectant Pontoon Side Keel (Port & Starboar... View Details

    View 15 Photos and Details Contact Seller
    $51,052
    VIEW DETAILS
  • 2026 Viaggio LAGO V22S TRITOON

    2026 Viaggio LAGO V22S TRITOON

    $54,573
    La Porte, IN

    The 2026 Viaggio Lago V22S Tritoon blends modern styling, upgraded comfort, and proven Viaggio performance—now available at Fay’s Marina in La Porte, Indiana 46350. Powered by the... View Details

    View 13 Photos and Details Contact Seller
    $54,573
    VIEW DETAILS
  • 2023 Manitou EXPLORE BENCH 22MAX STANDARD STEALTH

    2023 Manitou EXPLORE BENCH 22MAX STANDARD STEALTH

    $49,899
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22' / 0'
    • 2023 / Used
    • $49,899

    2023 Manitou Explore Bench 22 MAX – Standard Stealth only 23 HOURS!! Redefine your time on the water with the 2023 Manitou Explore Bench 22 MAX Standard Stealth. Engineered for thr... View Details

    View 19 Photos and Details Contact Seller
    $49,899
    VIEW DETAILS
  • Price Drop 2026 Viaggio LAGO V 22U TRITOON

    2026 Viaggio LAGO V 22U TRITOON

    $49,995
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22' / 9'
    • 2026 / New
    • $49,995

    New 2026 Viaggio Lago V22U TRITOON with BF 150 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. Upgrades include: Honda Pre-rig Cable Steering w/ Tilt Steering... View Details

    View 17 Photos and Details Contact Seller
    $49,995
    VIEW DETAILS
  • Price Drop 2026 Viaggio LAGO Z 22U TRITOON

    2026 Viaggio LAGO Z 22U TRITOON

    $68,749
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22' / 9'
    • 2026 / New
    • $68,749

    New 2026 Viaggio Lago Z22U Pontoon with BF 200 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. Upgrades include: Tube Protectant Pontoon Side Keel (Port & Starb... View Details

    View 14 Photos and Details Contact Seller
    $68,749
    VIEW DETAILS
  • Price Drop 2026 Viaggio LAGO X 22Q TRITOON

    2026 Viaggio LAGO X 22Q TRITOON

    $51,939
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22' / 9'
    • 2026 / New
    • $51,939

    New 2026 Viaggio Lago X22Q TRITOON with BF 140 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. ** Boat Show Savings + Honda Buyers Choice Sales Event Upgrades inc... View Details

    View 33 Photos and Details Contact Seller
    $51,939
    VIEW DETAILS
  • Price Drop 2026 Viaggio LAGO Z24U

    2026 Viaggio LAGO Z24U

    $85,399
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 24' / 9'
    • 2026 / New
    • $85,399

    New 2026 Viaggio Lago Z24U Tritoon with Honda BF250 for sale at Fay’s Marina in La Porte, Indiana. Loaded upgrades, premium Z Trim features, and performance Tritoon package. The 2... View Details

    View 1 Photo and Details Contact Seller
    $85,399
    VIEW DETAILS
  • Price Drop 2026 Viaggio LAGO X 22D TRITOON

    2026 Viaggio LAGO X 22D TRITOON

    $56,099
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22' / 9'
    • 2026 / New
    • $56,099

    New 2026 Viaggio Lago X22D TRITOON with BF 150 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. ** Boat Show Sale + :Honda Buyers Choice Sales Event Upgrades includ... View Details

    View 16 Photos and Details Contact Seller
    $56,099
    VIEW DETAILS
  • 1988 Four Winns 200 HORIZON

    1988 Four Winns 200 HORIZON

    $750
    La Porte, IN
    • La Porte, IN
    • Cruiser
    • 20' / 0'
    • 1988 / Used
    • $750

    1988 Four Winns 200 Horizon – DIY Project Opportunity with titles! A classic bowrider with restoration potential, this 1988 Four Winns 200 Horizon is ideal for hands-on boaters loo... View Details

    View 10 Photos and Details Contact Seller
    $750
    VIEW DETAILS
  • 2026 Scarab SB 210 LX

    2026 Scarab SB 210 LX

    $67,395
    La Porte, IN

    2026 Scarab 210 LX – Bold Performance Meets Refined Comfort Step into the next evolution of jet boating with the all-new 2026 Scarab 210 LX. Engineered for adrenaline and styled fo... View Details

    View 4 Photos and Details Contact Seller
    $67,395
    VIEW DETAILS
  • Price Drop 2026 Viaggio LAGO X 22S TRITOON

    2026 Viaggio LAGO X 22S TRITOON

    $57,269
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22' / 9'
    • 2026 / New
    • $57,269

    New 2026 Viaggio Lago X22S TRITOON with BF 150 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. ** Boat Show Savings + Honda Buyers Choice Sales Sales Event Upgrades... View Details

    View 16 Photos and Details Contact Seller
    $57,269
    VIEW DETAILS
  • 2019 Four Winns FL HD200 OB

    2019 Four Winns FL HD200 OB

    $29,900
    La Porte, IN
    • La Porte, IN
    • Cruiser
    • 20' / 0'
    • 2019 / Used
    • $29,900

    Turn heads with the 2019 Four Winns HD 200 deck boat, Mercury 200HP power, trailer included. Family‑ready, low hours, for sale at Fay’s Marina IN Experience the perfect blend of s... View Details

    View 27 Photos and Details Contact Seller
    $29,900
    VIEW DETAILS
  • 2022 Viaggio LAGO U 22

    2022 Viaggio LAGO U 22

    $35,999
    La Porte, IN

    Low-hour 2022 Viaggio Lago U22 Pontoon with Honda 90HP – only 67 hours! Spacious ‘U’ lounge, premium features, and ready for family fun. Available now at Fay’s Marina in La Porte,... View Details

    View 25 Photos and Details Contact Seller
    $35,999
    VIEW DETAILS
  • Price Drop 2018 Regal 28 Express

    2018 Regal 28 Express

    $119,900
    Newark, IL

    Stock #470421 Video of this vessel available at www [dot] popsells [dot] com/view/470421 Reason for selling is "not using enough". ANY and ALL offers will be put in front of our... View Details

    View 10 Photos and Details Contact Seller
    $119,900
    VIEW DETAILS
  • 1997 Bayliner 2655 Ciera

    1997 Bayliner 2655 Ciera

    $19,900
    Harvard, IL

    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

    View 10 Photos and Details Contact Seller
    $19,900
    VIEW DETAILS
  • 2023 Gala V330

    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

    View 3 Photos and Details Contact Seller
    $18,999
    VIEW DETAILS
  • 2023 Robalo R-266 Deepwater Black Wide Band

    2023 Robalo R-266 Deepwater Black Wide Band

    $149,900
    Racine, WI

    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

    View 21 Photos and Details Contact Seller
    $149,900
    VIEW DETAILS
  • 2025 Robalo Center Console R250

    2025 Robalo Center Console R250

    $193,625
    Racine, WI

    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

    View 23 Photos and Details Contact Seller
    $193,625
    VIEW DETAILS
  • 1986 Krogen 38 Cutter

    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

    View 56 Photos and Details Contact Seller
    $60,000
    VIEW DETAILS
Showing 526 to 546 of 1,208 boats found.
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