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 97 - 108 of 221 results
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Showing 97 - 108 of 221 results
  • FXD 2026 Super Glide®

    TB037560
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1BK915TB037560
    White Onyx Pearl
  • FXBR 2026 Breakout®

    TB028403
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YE91XTB028403
    Iron Horse Metallic Chrome Trim

    With 34 degrees of rake in the neck, a bobtail fender, and a 240mm rear tire, the 2026 Breakout  feels like a factory-built street sweeper. But don't get lost in the long-and-low chopper lore. This bike also offers USB-C charging, Rider Safety Enhancements standard, a monster Milwaukee-Eight® 117 …

  • FXBB 2026 Street Bob®

    TB038248
    New
    2026
    2 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJ917TB038248
    Aurora Blue Denim Chrome Cast Wheels

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®

    TB032271
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ915TB032271
    Olive Steel Metallic Chrome Cast Wheels

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®

    TB031346
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ915TB031346
    Vivid Black Chrome Cast Wheels

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®

    TB030057
    New
    2026
    6 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YJ914TB030057
    DRK BILIARD GRY

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®

    TB028876
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ918TB028876
    Vivid Black Chrome Cast Wheels

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®

    TB030033
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ911TB030033
    Olive Steel Metallic Chrome Laced Wheels

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®

    TB034400
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ910TB034400
    DRK BILIARD GRY

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®

    TB029196
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ912TB029196
    DRK BILIARD GRY

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®

    TB029201
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ912TB029201
    DRK BILIARD GRY

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®

    034340
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ918TB034340
    Vivid Black Chrome Cast Wheels

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.