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 109 - 120 of 221 results
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Showing 109 - 120 of 221 results
  • FXBB 2026 Street Bob®

    029312
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ910TB029312
    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®

    TB028903
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ917TB028903
    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®

    TB029435
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ915TB029435
    Vivid Black Black Two-Up 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®

    TB029048
    New
    2026
    2 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJ919TB029048
    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®

    TB032387
    New
    2026
    2 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJ912TB032387
    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®

    TB033070
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ910TB033070
    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®

    TB030066
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ915TB030066
    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®

    TB028222
    New
    2026
    4 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJ915TB028222
    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®

    TB032807
    New
    2026
    5 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ919TB032807
    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®

    TB025714
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ910TB025714
    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.

  • FLTRXSTSE 2026 CVO Road Glide ST

    TB956488
    New
    2026
    6 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1TL81XTB956488
    Inferno Gray

    The 2026 CVO Road Glide ST is Harley-Davidson’s race-inspired bagger at its most ruthless. Its Milwaukee-Eight® 121 High Output motor delivers unbelievable power and performance, fed by a Heavy Breather intake and finished with titanium-capped mufflers. Forged carbon fibre details, tall risers with …

  • FLTRXSTSE 2026 CVO Road Glide ST

    TB955463
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1TL810TB955463
    Electric Coast

    The 2026 CVO Road Glide ST is Harley-Davidson’s race-inspired bagger at its most ruthless. Its Milwaukee-Eight® 121 High Output motor delivers unbelievable power and performance, fed by a Heavy Breather intake and finished with titanium-capped mufflers. Forged carbon fibre details, tall risers with …