Discover our diverse selection of high-quality vehicles, from classic cars to modern marvels. Each vehicle is meticulously inspected to ensure top performance and reliability. Shop with confidence and drive away in the car of your dreams. Your satisfaction is our priority at Windy City Motors LLC.

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16%
Used 2019 Harley-Davidson® Cruiser MotorcycleFXBB – Softail Street Bob
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Used 2019 Harley-Davidson® Cruiser MotorcycleFXBB – Softail Street Bob

Original price was: $10,000.00.Current price is: $8,400.00.
  • Condition: Used
  • Year: 2019
  • Make: Harley-Davidson®
  • Model: FXBB - Softail® Street Bob®
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 6,321
  • Stock Number: 5622
  • Primary Color: Wicked Red & Twisted Cherry
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26%
Used 2019 Harley-Davidson Cruiser Street Bob®
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Used 2019 Harley-Davidson Cruiser Street Bob®

Original price was: $8,500.00.Current price is: $6,300.00.
  • Condition: Used
  • Year: 2019
  • Make: Harley-Davidson
  • Model: Street Bob®
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 1,024
  • Stock Number: U051469
  • VIN: 1HD1YJJ27KB051469
  • Primary Color: Wicked Red Denim
  • Engine Size: 1,746
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17%
Used 2019 Harley-Davidson Cruiser Sport Glide® For Sale
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Used 2019 Harley-Davidson Cruiser Sport Glide® For Sale

Original price was: $10,999.00.Current price is: $9,200.00.
  • Condition: Used
  • Year: 2019
  • Make: Harley-Davidson
  • Model: Sport Glide®
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 4,347
  • Stock Number: 065691B
  • VIN: 1HD1YMJ2XKB065691
  • Primary Color: Wicked Red
  • Engine Size: 1,746
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24%
Used 2023 Harley-Davidson® FXBBS – Street Bob® 114
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Used 2023 Harley-Davidson® FXBBS – Street Bob® 114

Original price was: $12,500.00.Current price is: $9,500.00.
  • Condition: Used
  • Year: 2023
  • Make: Harley-Davidson®
  • Model: FXBBS - Street Bob® 114
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 13,054
  • Stock Number: 023573
  • VIN: 1HD1YYK18PB023573
  • Primary Color: REDLINE RED
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42%
Used 2022 Harley-Davidson Nightster 975
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Used 2022 Harley-Davidson Nightster 975

Original price was: $5,950.00.Current price is: $3,500.00.
  • Condition: Used
  • Year: 2022
  • Make: Harley-Davidson
  • Model: Nightster 975
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 564
  • Stock Number: AV3516
  • VIN: 1HD1ZH117NB313296
  • Primary Color: Red
  • Engine Size: 975
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21%
Used 2021 Harley-Davidson SOFTAIL HERITAGE CLASSIC 114
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Used 2021 Harley-Davidson SOFTAIL HERITAGE CLASSIC 114

Original price was: $10,800.00.Current price is: $8,600.00.
  • Condition: Used
  • Year: 2021
  • Make: Harley-Davidson
  • Model: SOFTAIL HERITAGE CLASSIC 114
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 9,192
  • Stock Number: 050296
  • VIN: 1HD1YBK1XMB050296
  • Primary Color: Crimson/White
  • Engine Size: 1,868
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21%
Used 2020 Harley-Davidson Softail Heritage Classic 114 For Sale
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Used 2020 Harley-Davidson Softail Heritage Classic 114 For Sale

Original price was: $9,950.00.Current price is: $7,950.00.
  • ConditionUsed
  • Year2020
  • MakeHarley-Davidson
  • ModelSoftail Heritage Classic 114
  • CategoryCruiser
  • TypeMotorcycle
  • LocationZieglerville, PA
  • Mileage25,459
  • VIN1HD1YBK16LB025443
  • Primary ColorBilliard Red and Vivid Black
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20%
Used 2018 Harley-Davidson Cruiser Softail Sport Glide For Sale
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Used 2018 Harley-Davidson Cruiser Softail Sport Glide For Sale

Original price was: $7,500.00.Current price is: $6,000.00.
  • Condition: Used
  • Year: 2018
  • Make: Harley-Davidson
  • Model: Softail Sport Glide
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 45,858
  • VIN: 1HD1YMJ61JC080608
  • Primary Color: Twisted Cherry
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Used 2019 Harley-Davidson Cruiser Low Rider® For Sale
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Used 2019 Harley-Davidson Cruiser Low Rider® For Sale

$7,099.00
  • Condition: Used
  • Year: 2019
  • Make: Harley-Davidson
  • Model: Low Rider®
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 7,060
  • Stock Number: UM24387
  • Primary Color: Twisted Cherry
  • Engine Size: 1,746
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Used 2019 Harley-Davidson XL883N / Sportster (Iron 883)
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Used 2019 Harley-Davidson XL883N / Sportster (Iron 883)

$4,699.00
  • Condition: Used
  • Year: 2019
  • Make: Harley-Davidson
  • Model: XL883N / Sportster (Iron 883)
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 6,824
  • Engine Size: 883
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24%
Used 2023 Harley-Davidson® RH1250S – Sportster® S
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Used 2023 Harley-Davidson® RH1250S – Sportster® S

Original price was: $10,499.00.Current price is: $7,999.00.
  • Condition: Used
  • Year: 2023
  • Make: Harley-Davidson®
  • Model: RH1250S - Sportster® S
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 2,255
  • Stock Number: HD11188
  • VIN: 1HD1ZC413PB311188
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25%
Used 2023 Harley-Davidson® RH1250S – Sportster® S
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Used 2023 Harley-Davidson® RH1250S – Sportster® S

Original price was: $10,999.00.Current price is: $8,300.00.
  • Condition: Used
  • Year: 2023
  • Make: Harley-Davidson®
  • Model: RH1250S - Sportster® S
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 728
  • Stock Number: 316215
  • VIN: 1HD1ZC415PB316215
  • Primary Color: Bright Billiard Blue
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31%
Used 2020 Harley-Davidson® XL1200NS – Sportster® Iron 1200
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Used 2020 Harley-Davidson® XL1200NS – Sportster® Iron 1200

Original price was: $5,750.00.Current price is: $3,999.00.
  • Condition: Used
  • Year: 2020
  • Make: Harley-Davidson®
  • Model: XL1200NS - Sportster® Iron 1200
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 4,150
  • Stock Number: 430613P
  • VIN: 1HD1LP310LB430613
  • Primary Color: BILLIARD BLUE
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15%
Used 2023 Harley-Davidson® RH1250S – Sportster
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Used 2023 Harley-Davidson® RH1250S – Sportster

Original price was: $9,550.00.Current price is: $8,200.00.
  • Condition: Used
  • Year: 2023
  • Make: Harley-Davidson®
  • Model: RH975 - Nightster
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 12
  • Stock Number: U315508
  • Primary Color: REDLINE RED
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36%
Used 2023 Harley-Davidson® Sportbike Motorcycle
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Used 2023 Harley-Davidson® Sportbike Motorcycle

Original price was: $6,999.00.Current price is: $4,500.00.
  • Condition: Used
  • Year: 2023
  • Make: Harley-Davidson®
  • Model: RH975 - Nightster
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 5,569
  • Stock Number: TPB317756
  • Primary Color: RED
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38%
Used 2021 Harley-Davidson® Sportbike Motorcycle
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Used 2021 Harley-Davidson® Sportbike Motorcycle

Original price was: $7,399.00.Current price is: $4,599.00.
  • Condition: Used
  • Year: 2021
  • Make: Harley-Davidson®
  • Model: RH1250S - Sportster® S
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 7,026
  • Stock Number: TMB316016
  • Primary Color: WHITE
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26%
Used 2023 Harley-Davidson® Sportbike Motorcycle
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Used 2023 Harley-Davidson® Sportbike Motorcycle

Original price was: $8,999.00.Current price is: $6,700.00.
  • Condition: Used
  • Year: 2023
  • Make: Harley-Davidson®
  • Model: RH1250S - Sportster® S
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 831
  • Stock Number: P311354
  • VIN: 1HD1ZC424PB311354
  • Primary Color: WHITE SAND PERAL
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22%
Used 2021 Harley-Davidson® Sportbike Motorcycle
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Used 2021 Harley-Davidson® Sportbike Motorcycle

Original price was: $12,500.00.Current price is: $9,750.00.
  • Condition: Used
  • Year: 2021
  • Make: Harley-Davidson®
  • Model: Pan America 1250 Special
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 390
  • Stock Number: X305109
  • Primary Color: BAJA ORANGE/STONE WASHED WH
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Used 2020 Harley-Davidson® Sportbike Motorcycle
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Used 2020 Harley-Davidson® Sportbike Motorcycle

  • Condition: Used
  • Year: 2020
  • Make: Harley-Davidson®
  • Model: XL883N - Sportster® Iron 883
  • Category: Sportbike
  • Type: Motorcycle
  • Mileage: 1,840
  • Stock Number: 410608P
  • VIN: 1HD4LE212LB410608
  • Primary Color: BARRACUDA SILVER DENIM
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Used 2021 Harley-Davidson® Cruiser Motorcycle
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Used 2021 Harley-Davidson® Cruiser Motorcycle

$9,500.00
  • Condition: Used
  • Year: 2021
  • MakeHarley-Davidson®
  • ModelXL883N - Iron 883
  • CategoryCruiser
  • TypeMotorcycle
  • LocationPoughkeepsie, NY
  • Mileage3,225
  • Stock Number1HD4LE21XMB406548
  • VIN1HD4LE21XMB406548
  • Primary ColorBLK
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34%
Used 2022 Harley-Davidson Cruiser Motorcycle
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Used 2022 Harley-Davidson Cruiser Motorcycle

Original price was: $15,750.00.Current price is: $10,500.00.
  • Condition: Used
  • Year: 2022
  • Make: Harley-Davidson
  • Model: STREET GLIDE
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 25
  • VIN: 1HD1KBC18NB670100
  • Primary Color: Black
  • Secondary Color: Black
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36%
Used 2019 Harley-Davidson Cruiser Motorcycle
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Used 2019 Harley-Davidson Cruiser Motorcycle

Original price was: $16,999.00.Current price is: $11,000.00.
  • Condition: Used
  • Year: 2019
  • Make: Harley-Davidson
  • Model: FLHXS Street Glide Special
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 6,532
  • Stock Number: 19FLHXS-304
  • Primary Color: Black
  • Secondary Color: Blue
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40%
Used 2020 Harley-Davidson® Cruiser Motorcycle
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Used 2020 Harley-Davidson® Cruiser Motorcycle

Original price was: $6,950.00.Current price is: $4,200.00.
  • Condition: Used
  • Year: 2020
  • Make: Harley-Davidson®
  • Model: XL883N - Sportster® Iron 883
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 1,693
  • Stock Number: 5501
  • Primary Color: Black Denim
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21%
Used 2023 Harley-Davidson® Cruiser Motorcycle
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Used 2023 Harley-Davidson® Cruiser Motorcycle

Original price was: $11,999.00.Current price is: $9,500.00.
  • Condition: Used
  • Year: 2023
  • Make: Harley-Davidson®
  • Model: FXBBS - Street Bob® 114
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 130
  • Stock Number: 5933A
  • Primary Color: BLACK
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19%
Used 2022 Harley-Davidson Cruiser Motorcycle
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Used 2022 Harley-Davidson Cruiser Motorcycle

Original price was: $13,500.00.Current price is: $11,000.00.
  • Condition: Used
  • Year: 2022
  • Make: Harley-Davidson
  • Model: Fat Bob 114
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 46
  • Stock Number: 022651UH
  • Primary Color: Vivid Black
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23%
Used 2020 Harley-Davidson Cruiser Motorcycle
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Used 2020 Harley-Davidson Cruiser Motorcycle

Original price was: $13,500.00.Current price is: $10,500.00.
  • Condition: Used
  • Year: 2020
  • Make: Harley-Davidson
  • Model: Low Rider®S
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 8,442
  • Stock Number: T65087
  • VIN: 1HD1YWK12LB065087
  • Primary Color: Vivid Black
  • Engine Size: 1,868
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35%
Used 2021 Harley-Davidson Cruiser Motorcycle
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Used 2021 Harley-Davidson Cruiser Motorcycle

Original price was: $7,500.00.Current price is: $4,900.00.
  • Condition: Used
  • Year: 2021
  • Make: Harley-Davidson
  • Model: Softail® Standard
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 2,777
  • Stock Number: N/A
  • Primary Color: Vivid Black
  • Engine Size: 1,746
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26%
Used 2019 Harley-Davidson Cruiser Motorcycle
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Used 2019 Harley-Davidson Cruiser Motorcycle

Original price was: $8,950.00.Current price is: $6,700.00.
  • Condition: Used
  • Year: 2019
  • Make: Harley-Davidson
  • Model: Street Bob®
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 11,079
  • Stock Number: N/A
  • Primary Color: Vivid Black
  • Engine Size: 1,746
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23%
Used 2023 Harley-Davidson Cruiser Motorcycle
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Used 2023 Harley-Davidson Cruiser Motorcycle

Original price was: $10,999.00.Current price is: $8,500.00.
  • Condition: Used
  • Year: 2023
  • Make: Harley-Davidson
  • Model: Street Bob® 114
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 648
  • Stock Number: N/A
  • Primary Color: Vivid Black
  • Engine Size: 1,868
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25%
Used 2019 Harley-Davidson Cruiser Motorcycle
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Used 2019 Harley-Davidson Cruiser Motorcycle

Original price was: $7,300.00.Current price is: $5,500.00.
  • Condition: Used
  • Year: 2019
  • Make: Harley-Davidson
  • Model: STREET BOB 114
  • Category: Cruiser
  • Type: Motorcycle
  • Mileage: 7,963
  • VIN: 1HD1YJJ12KC022317
  • Primary Color: Black
  • Engine Size: 1,868
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