Windy City Harley-Davidson® 14000 W Rockland Rd, Green Oaks, IL 60048
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(847) 662-4500
(847) 662-4500

NEW HARLEY-DAVIDSON® MOTORCYCLE INVENTORY


Explore new 2025 & 2026 Harley-Davidson® models for sale at Windy City Harley-Davidson® in Libertyville, IL

Find your next new motorcycle when you work with the experts at Windy City Harley-Davidson®! We offer a huge selection of hundreds of new bikes for sale, so we're sure to have something in stock to fit your riding needs!

Why Buy From Us?

Anyone can sell you a motorcycle. What sets us apart is what happens after. We believe in treating people like family, not numbers, and making sure every rider feels supported long after they leave the showroom. From service and parts to events and community, we’re here for the long haul — because your experience shouldn’t end when the sale does.

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Showing 265 - 276 of 467 results
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Showing 265 - 276 of 467 results
  • Harley-Davidson® Breakout® 2016 FXSB BILLET SILVER

    Harley-Davidson® Breakout® 2016 FXSB BILLET SILVER $20,199.00 $14,999.00

    036562
    Pre-owned
    2016
    2670 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BFV10GB036562
    Billet Silver

    Feast your eyes on the Breakout™ motorcycle’s glittering new High Output Twin Cam 103™ engine, waiting to send mountains of torque to that meaty 240mm rear tire. The profile is low, stretched out and undeniably aggressive. We top it with drag bars. This one lives to defy gravity and everything else.

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  • FXSB 2016 Breakout®

    FXSB 2016 Breakout® $18,699.00 $12,999.00

    037767
    Pre-owned
    2016
    6951 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1BFV11GB037767
    Vivid Black

    Feast your eyes on the Breakout™ motorcycle’s glittering new High Output Twin Cam 103™ engine, waiting to send mountains of torque to that meaty 240mm rear tire. The profile is low, stretched out and undeniably aggressive. We top it with drag bars. This one lives to defy gravity and everything else.

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  • FXDB 2016 Street Bob®

    FXDB 2016 Street Bob® $13,699.00 $10,995.00

    302910
    Pre-owned
    2016
    6749 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1GXM19GC302910
    Olive Gold

    The original bobber fanatics invented the style you see here, and they had one rule: if it weighs you down, get rid of it. That’s the Street Bob® motorcycle in spades. Solo seat. Chopped rear fender. Mini-apes putting your fists in the wind. All it takes is a twist of the wrist to send whatever the …

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  • FLTRXS 2016 Road Glide® Special

    FLTRXS 2016 Road Glide® Special

    691111
    Pre-owned
    2016
    36351 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1KTM19GB691111
    BLACK QUARTZ

    Like the rock that diverts the mainstream, our frame-mounted Road Glide® Special motorcycle fairing splits the wind and conventional opinion alike. This is an exercise in how far you can take a motorcycle in terms of miles, attitude and function. You’ve got all the Project RUSHMORE …

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  • FLSTN 2016 Softail® Deluxe

    FLSTN 2016 Softail® Deluxe $19,949.00 $14,999.00

    GB041349
    Pre-owned
    2016
    7342 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1JDV14GB041349
    Two-Tone Mysterious Red Sunglo/Velocity Red Sunglo

    There aren’t that many things left in this world that make a hard-working man or woman feel truly deluxe. This motorcycle is one of them. Roll into town and you can feel the eyes on the chrome and laced wheels, wrapped in whitewall tires. The full-skirted metal fenders. The big chromed headlamp and …

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  • FLSTC 2016 Heritage Softail® Classic

    FLSTC 2016 Heritage Softail® Classic $17,349.00 $12,495.00

    041206
    Pre-owned
    2016
    22295 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1BWV31GB041206
    Superior Blue

    The Heritage Softail® Classic drips with the nostalgia of days gone by, but that’s only half of the equation for the rider of today. The hidden suspension gives you the authentic look without the bone-shaking ride of an old Hardtail. You get the comfort of cruise control for those long stretches of …

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  • FLHXSE 2016 CVO™ Street Glide®

    FLHXSE 2016 CVO™ Street Glide® $36,999.00 $23,999.00

    954420
    Pre-owned
    2016
    53054 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1PXN12GB954420
    Black Licorice with Midnight Cobalt Flames

    Let’s say you want to ride into Bike Week with a full-on custom look that drops jaws and pops eyes all along Main Street. But you also like a machine that’s built tight and right with all the latest in refined technology and touring comfort. And let’s say you want it all built around 110 cubic …

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  • FLHXSE 2016 CVO™ Street Glide®

    FLHXSE 2016 CVO™ Street Glide® $36,999.00 $22,999.00

    950336
    Pre-owned
    2016
    18710 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1PXN14GB950336
    CRB CRY/PTM FLM

    Let’s say you want to ride into Bike Week with a full-on custom look that drops jaws and pops eyes all along Main Street. But you also like a machine that’s built tight and right with all the latest in refined technology and touring comfort. And let’s say you want it all built around 110 cubic …

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  • FLHXSE 2016 CVO™ Street Glide®

    FLHXSE 2016 CVO™ Street Glide® $26,799.00 $21,999.00

    956322
    Pre-owned
    2016
    12774 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1PXN11GB956322
    CRB CRY/PTM FLM

    Let’s say you want to ride into Bike Week with a full-on custom look that drops jaws and pops eyes all along Main Street. But you also like a machine that’s built tight and right with all the latest in refined technology and touring comfort. And let’s say you want it all built around 110 cubic …

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  • FLHXSE 2016 CVO™ Street Glide®

    FLHXSE 2016 CVO™ Street Glide® $36,799.00 $22,999.00

    954104
    Pre-owned
    2016
    6215 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1PXN13GB954104
    BLK LIC/MDNTCBT W/PINSTRIPE

    Let’s say you want to ride into Bike Week with a full-on custom look that drops jaws and pops eyes all along Main Street. But you also like a machine that’s built tight and right with all the latest in refined technology and touring comfort. And let’s say you want it all built around 110 cubic …

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  • FLHXS 2016 Street Glide® Special

    FLHXS 2016 Street Glide® Special $26,399.00 $16,999.00

    687272
    Pre-owned
    2016
    5500 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1KRM19GB687272
    Deep Jade Pearl

    You’re looking at the answer to the question, how do you fully load a touring bike with premium features and still roll with the stripped down bagger look? Check inside the sleek Project RUSHMORE batwing fairing and you’ll get an idea. Your looking at the top-of-the-line 6.5 inch touchscreen …

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  • FLHTK 2016 Ultra Limited

    FLHTK 2016 Ultra Limited $26,999.00 $14,499.00

    684281
    Pre-owned
    2016
    39012 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KEL13GB684281
    2T RED

    Here's what you get with The Project RUSHMORE Ultra touring experience: Every idea millions of miles of riding and hundreds of conversations with riders could dream up and build into a horizon hunting machine. Like saddlebags that open with one touch. A fairing that reduces head buffeting. More …

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