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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41%
Used 2021 Yamaha Standard MT 07 For Sale
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Used 2021 Yamaha Standard MT 07 For Sale

Original price was: $5,900.00.Current price is: $3,500.00.

  • Condition: Used
  • Year: 2021
  • Make: Yamaha
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17%
Used 2020 Yamaha Sportbike MT-10 For Sale
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Used 2020 Yamaha Sportbike MT-10 For Sale

Original price was: $9,500.00.Current price is: $7,950.00.

  • Condition: Used
  • Year: 2020
  • Make: Yamaha
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22%
Used 2018 Yamaha MT -09 For Sale
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Used 2018 Yamaha MT -09 For Sale

Original price was: $7,500.00.Current price is: $5,900.00.

  • Condition: Used
  • Year: 2018
  • Make: Yamaha
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New 2023 Yamaha Cruiser Bolt R-Spec For Sale
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New 2023 Yamaha Cruiser Bolt R-Spec For Sale

$4,100.00

  • Condition: New
  • Year: 2023
  • Make: Yamaha
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14%
New 2022 Yamaha Touring Tracer 9 GT For Sale
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New 2022 Yamaha Touring Tracer 9 GT For Sale

Original price was: $9,500.00.Current price is: $8,200.00.

  • Condition: New
  • Year: 2022
  • Make: Yamaha
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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®
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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
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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
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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®
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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
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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
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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
  • Model
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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
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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
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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
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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®
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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®
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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®
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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®
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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®
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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®
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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®
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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®
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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®
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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®
  • Model
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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
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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
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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®
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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®
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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
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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
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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
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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
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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
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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
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