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Boats for sale in Chicago Illinois

There are 460 new and used boats for sale in Chicago, Illinois. Browse Pontoon, Cruiser, Bowrider, Fishing, Ski & Wake, and Center Console from brands like Sea Ray, Harris, Scout, Mastercraft, Aviara, and Bayliner on BoatCrazy. View a wide selection of boats from $100 to $585,211.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
460 boats found within 100 miles out of 11,722 Boats Found
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  • 2025 Viaggio LAGO V 20U

    2025 Viaggio LAGO V 20U

    $40,093
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 20'
    • 2025 / New
    • $40,093

    New 2025 Viaggio Lago V20U Pontoon with BF 50 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. Standard Features Exclusive Matte Metallic Fencing (Standard Colors On... View Details

    View 16 Photos and Details Contact Seller
    $40,093
    VIEW DETAILS
  • Price Drop 1988 Four Winns 200 HORIZON

    1988 Four Winns 200 HORIZON

    $500
    La Porte, IN
    • La Porte, IN
    • Cruiser
    • 20'
    • 1988 / Used
    • $500

    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 lo... View Details

    View 10 Photos and Details Contact Seller
    $500
    VIEW DETAILS
  • 2026 Viaggio LAGO X 22Q TRITOON

    2026 Viaggio LAGO X 22Q TRITOON

    $51,939
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22'
    • 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
  • 2026 Viaggio LAGO Z 22U TRITOON

    2026 Viaggio LAGO Z 22U TRITOON

    $68,749
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22'
    • 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
  • 2025 Viaggio LAGO V 20U

    2025 Viaggio LAGO V 20U

    $41,866
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 20'
    • 2025 / New
    • $41,866

    New 2025 Viaggio Lago V20U Pontoon with BF 90 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. Upgrades include: Honda Pre-rig, Boss MGR350B Reciever and 2 Marine Spea... View Details

    View 14 Photos and Details Contact Seller
    $41,866
    VIEW DETAILS
  • 2025 Viaggio LAGO X 20U

    2025 Viaggio LAGO X 20U

    $39,999
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 20'
    • 2025 / New
    • $39,999

    New Viaggio Lago X20U Pontoon with BF 90 HP Honda Motor for Sale Fay's Marina La Porte Indiana 46350. Upgrades include: Honda Pre-rig Boss MGR350B Reciever and 2 Marine Spea... View Details

    View 14 Photos and Details Contact Seller
    $39,999
    VIEW DETAILS
  • 2026 Viaggio LAGO V 22U TRITOON

    2026 Viaggio LAGO V 22U TRITOON

    $49,995
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22'
    • 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 2025 Scarab 215 ID T170 DIGITAL SPEED CONTROL PKG

    2025 Scarab 215 ID T170 DIGITAL SPEED CONTROL PKG

    $54,880
    La Porte, IN
    • La Porte, IN
    • Jet boat
    • 21'
    • 2025 / New
    • $54,880

    Scarab 215 ID (LX) T170 340hp Full Throttle Savings Event at Fay’s Marina, La Porte, Indiana MSRP $87,352 SALE PRICED $54,880 + frt prep title tax, with $8,000 July Full Throttle... View Details

    View 19 Photos and Details Contact Seller
    $54,880
    VIEW DETAILS
  • Price Drop 2022 Coach 221 RFC 1-SERIES SPORTTOON

    2022 Coach 221 RFC 1-SERIES SPORTTOON

    $42,750
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 21'
    • 2022 / New
    • $42,750

    SAVE BIG WITH FAY'S CLEAR THE DECKS FINAL CLEARANCE SALE! MSRP -- $78,157 CLEAR THE DECKS FOR NEW MODELS -- $42,750 + frt & prep - WHY BUY USED WHEN YOU CAN BUY NEW WITH 5-YEAR... View Details

    View 24 Photos and Details Contact Seller
    $42,750
    VIEW DETAILS
  • Price Drop 2025 Scarab 215 ID (LX) T230 PREMIUM SOUND

    2025 Scarab 215 ID (LX) T230 PREMIUM SOUND

    $67,890
    La Porte, IN
    • La Porte, IN
    • Jet boat
    • 21'
    • 2025 / New
    • $67,890

    New Scarab 215 ID LX, T230 (460 HP) Twin Rotax Jet Boat, with Premium Sound, Impact Graphics & mats, RGB lighting, trailer and more! High-performance jet boat available now at Fay’... View Details

    View 2 Photos and Details Contact Seller
    $67,890
    VIEW DETAILS
  • 2023 Viaggio DIAMANTE D 23S TRITOON

    2023 Viaggio DIAMANTE D 23S TRITOON

    $70,370
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 23'
    • 2023 / New
    • $70,370

    FAYS CLEAR THE DECKS FINAL CLEARANCE ON LUXURY TRI-TOON PONTOONS! New Viaggio Diamante D23S Tri Toon, Full Platinum Package, Power Bimini, Power Steering, BF250 hp Honda, More, Fa... View Details

    View 41 Photos and Details Contact Seller
    $70,370
    VIEW DETAILS
  • 2007 Bayliner 195BR

    2007 Bayliner 195BR

    $9,500
    La Porte, IN
    • La Porte, IN
    • Bowrider
    • 0'
    • 2007 / Used
    • $9,500

    2007 Bayliner 195 Bowrider – Clean, Versatile, and Ready for the Water This 2007 Bayliner 195 BR is a solid, family-friendly bowrider with the power and layout to handle everythin... View Details

    View 18 Photos and Details Contact Seller
    $9,500
    VIEW DETAILS
  • 2021 Malibu 22 LSV

    2021 Malibu 22 LSV

    $109,000
    Barrington, IL
    • Barrington, IL
    • Ski & Wake
    • 22'
    • 2021 / Used
    • $109,000

    Stock #342618 Video of this vessel available at www [dot] popsells [dot] com/view/342618 Reason for selling is "No longer uses it.". ANY and ALL offers will be put in front of o... View Details

    View 10 Photos and Details Contact Seller
    $109,000
    VIEW DETAILS
  • 2023 Monterey M20

    2023 Monterey M20

    $67,900
    Mundelein, IL
    • Mundelein, IL
    • Bowrider
    • 20'
    • 2023 / Used
    • $67,900

    Stock #482891 Video of this vessel available at www [dot] popsells [dot] com/view/482891 Reason for selling is "Relocating". This Monterey has been on the market for more than 3... View Details

    View 10 Photos and Details Contact Seller
    $67,900
    VIEW DETAILS
  • Price Drop 1983 Sea Ray 390 Sportfish

    1983 Sea Ray 390 Sportfish

    $33,500
    Waukegan, IL

    Stock #490810 Video of this vessel available at www [dot] popsells [dot] com/view/490810 Reason for selling is "No longer using it enough". This Sea Ray has been on the market f... View Details

    View 10 Photos and Details Contact Seller
    $33,500
    VIEW DETAILS
  • Price Drop 2000 Sea Ray 280 Sun Sport

    2000 Sea Ray 280 Sun Sport

    $29,800
    Waukegan, IL

    Stock #489713 Video of this vessel available at www [dot] popsells [dot] com/view/489713 Reason for selling is "No longer using it enough". This Sea Ray has now been on the mark... View Details

    View 10 Photos and Details Contact Seller
    $29,800
    VIEW DETAILS
  • 2018 Crownline 264 CR

    2018 Crownline 264 CR

    $68,000
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 26'
    • 2018 / Used
    • $68,000

    Trailer Included! Priced to sell! Great opprotunity! Powered by a MerCruiser 6.2L MPI 300 HP V8 with a Bravo III dual-prop drive, the 264 CR delivers smooth handling, strong perfor... View Details

    View 15 Photos and Details Contact Seller
    $68,000
    VIEW DETAILS
  • 2026 Sea Ray Sundancer 320 Outboard

    2026 Sea Ray Sundancer 320 Outboard

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 32'
    • 2026 / New
    • Call for price

    Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat from any participating SkipperBud's locati... View Details

    View 30 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Saxdor 320 GTC

    2026 Saxdor 320 GTC

    Call for price
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 32'
    • 2026 / New
    • Call for price

    Act fast on this limited-time offer! Free Winterization, Shrink Wrap & Outside Storage Offer Terms:Offer valid with the purchase of an eligible new or pre-owned boat from any p... View Details

    View 30 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 1996 Sea Ray 290 SUNDANCER

    1996 Sea Ray 290 SUNDANCER

    $34,900
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Cruiser
    • 29'
    • 1996 / Used
    • $34,900

    Ready for viewing, , Upgraded, Cleaned, 680 Engine Hours, Turn Key!!! Experience timeless styling, impressive performance, and exceptional care with this 1996 Sea Ray 290 Sundancer... View Details

    View 25 Photos and Details Contact Seller
    $34,900
    VIEW DETAILS
  • 1978 Bertram 31

    1978 Bertram 31

    $119,900
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Yacht
    • 31'
    • 1978 / Used
    • $119,900

    Listing Title: 1978 Bertram 31 Unmatched Performance Experience the thrill of the open water with the 1978 Bertram 31, powered by twin MERCRUISER 7.4L engines delivering a combined... View Details

    View 30 Photos and Details Contact Seller
    $119,900
    VIEW DETAILS
Showing 22 to 42 of 460 boats found.
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