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Boats for sale in Chicago Illinois

There are 1218 new and used boats for sale in Chicago, Illinois. Browse Pontoon, Fishing, Cruiser, Center Console, Runabout, and Ski & Wake from brands like Scout, Sea Ray, Yamaha, Harris, Barletta, and Bayliner on BoatCrazy. View a wide selection of boats from $300 to $2,549,000.
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  • Boats
  • Within 100 Miles Of
    Chicago, Illinois
1,218 boats found within 100 miles from Chicago, Illinois
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  • 2023 Nautic Star 203 DC

    2023 Nautic Star 203 DC

    $43,900
    Antioch, IL

    2023 Nautic Star 203DC 20' Deck Boat, Mercury 115hp ProXS O/B, Single Axle Trailer w/spare tire & swing tongue, ext engine warranty until 12/27/2027 (buyer pays to transfer) wa... View Details

    View 30 Photos and Details Contact Seller
    $43,900
    VIEW DETAILS
  • Price Drop 2022 Coach 221 RFC 1-SERIES SPORTTOON

    2022 Coach 221 RFC 1-SERIES SPORTTOON

    $43,990
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 21'
    • 2022 / New
    • $43,990

    Save Big with Fay's Marina Clearance Sale! MSRP $78,157 CLEARANCE SALE {WHY BUY USED WHEN NEW 5-YEAR HONDA WARRANTY?} New Coach 221 RFC White Diamond Sport Tritoon available now... View Details

    View 24 Photos and Details Contact Seller
    $43,990
    VIEW DETAILS
  • Price Drop 2023 Bayliner DX 2050 (D20i)

    2023 Bayliner DX 2050 (D20i)

    $43,990
    La Porte, IN
    • La Porte, IN
    • Deck Boat
    • 20'
    • 2023 / New
    • $43,990

    Shop the Bayliner DX 2050 (D20i) Deck Boat at Fay’s Marina in La Porte, Indiana. Powered by a 200HP MerCruiser stern drive with Full Windshield Dual Consoles, Comfort Package, Pro... View Details

    View 40 Photos and Details Contact Seller
    $43,990
    VIEW DETAILS
  • Price Drop 2022 Coach 221 RFC 1-SERIES SPORTTOON

    2022 Coach 221 RFC 1-SERIES SPORTTOON

    $43,990
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 21'
    • 2022 / New
    • $43,990

    SAVE BIG WITH FAY'S FINAL CLEARANCE SALE! MSRP $77,564 | WHY BUY USED WHEN YOU HAVE 5 YEAR NEW HONDA WARRANTY? 2022 Coach 221 RFC Sport Tri Toon available now at Fay's Marina LaP... View Details

    View 32 Photos and Details Contact Seller
    $43,990
    VIEW DETAILS
  • Price Drop 2022 Coach 221 RFC 1-SERIES SPORTTOON

    2022 Coach 221 RFC 1-SERIES SPORTTOON

    $43,990
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 21'
    • 2022 / New
    • $43,990

    SAVE BIG WITH FAY'S FINAL CLEARANCE SALE MSRP $77,606.00 > WHY BUY USED WHEN NEW 5-YEAR HONDA WARRANTY! New Coach 221 RFC SportToon available now at Fay's Marina LaPorte Indiana... View Details

    View 30 Photos and Details Contact Seller
    $43,990
    VIEW DETAILS
  • Price Drop 2022 Coach 221 RFC 1-SERIES SPORTTOON

    2022 Coach 221 RFC 1-SERIES SPORTTOON

    $43,990
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 21'
    • 2022 / New
    • $43,990

    SAVE BIG WITH FAY'S FINAL CLEARANCE SALE! MSRP $77,606.00 | SAVE! {WHY BUY USED WHEN YOU CAN HAVE 5-YEAR NEW HONDA WARRANTY?} New Coach 221 RFC Sport Tri Toon With BF 150 Hp Hond... View Details

    View 36 Photos and Details Contact Seller
    $43,990
    VIEW DETAILS
  • 2019 Glastron 225 GTS

    2019 Glastron 225 GTS

    $43,995
    Pewaukee, WI
    • Pewaukee, WI
    • Deck Boat
    • 22'
    • 2019 / Used
    • $43,995

    2019 Glastron 225 GTS View Details

    View 11 Photos and Details Contact Seller
    $43,995
    VIEW DETAILS
  • 2004 Chaparral 280 SSi

    2004 Chaparral 280 SSi

    $44,000
    Waterford, WI
    • Waterford, WI
    • Bowrider
    • 28'
    • 2004 / Used
    • $44,000

    Stock #487201 Video of this vessel available at www [dot] popsells [dot] com/view/487201 Reason for selling is "Buying a smaller boat". This Chaparral has been on the market for... View Details

    View 10 Photos and Details Contact Seller
    $44,000
    VIEW DETAILS
  • 2026 Starcraft SVX 171 OB

    2026 Starcraft SVX 171 OB

    $44,129
    Pewaukee, WI
    • Pewaukee, WI
    • Deck Boat
    • 17'
    • 2026 / New
    • $44,129

    Act fast on this limited-time offer! In the SVX 171 OB deckboat by Starcraft, there’s something for everyone — whether you love cruising, watersports or simply hanging out at the s... View Details

    View 4 Photos and Details Contact Seller
    $44,129
    VIEW DETAILS
  • 2026 Starcraft SVX 171 OB

    2026 Starcraft SVX 171 OB

    $44,820
    Antioch, IL
    • Antioch, IL
    • Deck Boat
    • 17'
    • 2026 / New
    • $44,820

    Act fast on this limited-time offer! In the SVX 171 OB deckboat by Starcraft, there’s something for everyone — whether you love cruising, watersports or simply hanging out at the s... View Details

    View 15 Photos and Details Contact Seller
    $44,820
    VIEW DETAILS
  • Price Drop 2022 Coach 243 RFC 3-SERIES

    2022 Coach 243 RFC 3-SERIES

    $44,990
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 25'
    • 2022 / New
    • $44,990

    New Coach 243 RFC Blackout Deluxe Package Bitoon with BF150 hp Honda. MSRP $72,730 - CLEARANCE SALE - Why buy Used when Clearance-Priced New with 5 Year Honda Warranty? New Coach... View Details

    View 45 Photos and Details Contact Seller
    $44,990
    VIEW DETAILS
  • 2025 Starcraft GX 22 R DH SPORT

    2025 Starcraft GX 22 R DH SPORT

    $44,995
    Leesburg, IN
    • Leesburg, IN
    • Pontoon
    • 22'
    • 2025 / New
    • $44,995

    The Starcraft Pontoon GX 22 R DH Sport is the ultimate choice for water enthusiasts, combining style and functionality with top-notch performance. Built on robust 23-inch diameter... View Details

    View 12 Photos and Details Contact Seller
    $44,995
    VIEW DETAILS
  • 2026 Starcraft SVX 171 OB

    2026 Starcraft SVX 171 OB

    $45,204
    Pewaukee, WI
    • Pewaukee, WI
    • Deck Boat
    • 17'
    • 2026 / New
    • $45,204

    Act fast on this limited-time offer! In the SVX 171 OB deckboat by Starcraft, there’s something for everyone — whether you love cruising, watersports or simply hanging out at the s... View Details

    View 4 Photos and Details Contact Seller
    $45,204
    VIEW DETAILS
  • 2025 Bayliner D20

    2025 Bayliner D20

    $45,945
    Antioch, IL
    • Antioch, IL
    • Deck Boat
    • 20'
    • 2025 / New
    • $45,945

    Contact us to find out ALL available savings! Act fast on this limited-time offer! The D20 outboard model is perfect for families looking for versatility and comfort on the water.... View Details

    View 30 Photos and Details Contact Seller
    $45,945
    VIEW DETAILS
  • Price Drop 2023 Manitou EXPLORE BENCH 22MAX STANDARD STEALTH

    2023 Manitou EXPLORE BENCH 22MAX STANDARD STEALTH

    $45,999
    La Porte, IN
    • La Porte, IN
    • Pontoon
    • 22'
    • 2023 / Used
    • $45,999

    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
    $45,999
    VIEW DETAILS
  • 2005 Formula 260 Bowrider

    2005 Formula 260 Bowrider

    $46,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Runabout
    • 26'
    • 2005 / Used
    • $46,900

    Chase sunsets with this 2005 Formula 260 Bowrider, a premium sport boat built for performance, comfort, and luxury. A top brand known for its superior handling, quality constructio... View Details

    View 31 Photos and Details Contact Seller
    $46,900
    VIEW DETAILS
  • 2016 Tige R20

    2016 Tige R20

    $47,149
    Antioch, IL

    Unleash endless fun on the water with the 2016 Tigé R20—a wake and surf machine built for unforgettable adventures around SkipperBuds Antioch. Powered by the Indmar 360 engine, thi... View Details

    View 30 Photos and Details Contact Seller
    $47,149
    VIEW DETAILS
  • 2026 Starcraft VX 22 Q DH

    2026 Starcraft VX 22 Q DH

    $47,434
    Pewaukee, WI
    • Pewaukee, WI
    • Pontoon
    • 22'
    • 2026 / New
    • $47,434

    Act fast on this limited-time offer! Introducing the 2026 Starcraft VX 22 Q DH Experience the perfect blend of luxury and performance with the stunning 2026 Starcraft VX 22 Q DH, a... View Details

    View 17 Photos and Details Contact Seller
    $47,434
    VIEW DETAILS
  • 2025 Bayliner D20

    2025 Bayliner D20

    $47,447
    Pewaukee, WI
    • Pewaukee, WI
    • Deck Boat
    • 20'
    • 2025 / New
    • $47,447

    Contact us to find out ALL available savings! Act fast on this limited-time offer! The D20 outboard model is perfect for families looking for versatility and comfort on the water.... View Details

    View 16 Photos and Details Contact Seller
    $47,447
    VIEW DETAILS
  • 2026 Barletta Aria 20 L

    2026 Barletta Aria 20 L

    $47,861
    Pewaukee, WI
    • Pewaukee, WI
    • Pontoon
    • 21'
    • 2026 / New
    • $47,861

    Experience Unmatched Luxury Step aboard the stunning 2026 Barletta ARIA20L, a vessel that blends exquisite craftsmanship with unparalleled performance. This new luxury boat, locate... View Details

    View 8 Photos and Details Contact Seller
    $47,861
    VIEW DETAILS
  • 2010 Mastercraft x15

    2010 Mastercraft x15

    $47,995
    Leesburg, IN
    • Leesburg, IN
    • Wakeboard
    • 22'
    • 2010 / Used
    • $47,995

    2010 MASTERCRAFT X15 POWERED BY 350 MOTOR EFI MOTOR. TANDEM AXLE TRAILER. COVER. MORE PICTURES COMING SOON BOAT IS CURRENTLY INSIDE STORED.. APPROX 500 HOURS. Length Overall: 21 ft... View Details

    View 13 Photos and Details Contact Seller
    $47,995
    VIEW DETAILS
Showing 148 to 168 of 1,218 boats found.
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