Used Powersports For Sale in Chicago, Milwaukee & Detroit
Windy City Motorcycle Company Inventory
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$317Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2023 Harley-Davidson® FLHXS - Street Glide® Special
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U674656-MKE -
Vin
1HD1KRP11PB674656 -
Vehicle Type
Motorcycle / Scooter -
Category
Touring -
Odometer
1469 -
Color
Vivid Black -
Family
Grand American Touring
2023 Harley-Davidson® Street Glide® Special A factory-custom bagger with highway-shredding power, in a blacked-out or chrome finish. Features may include: Milwaukee-Eight 114 V-Twin engine and Prodigy™ wheels Never before offered two-tone paint schemes Bright white Daymaker LED headlamp STRETCHED SADDLEBAGS Designed to accentuate the long and low ...
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$146Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2022 Harley-Davidson® FXST - Softail® Standard
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U023737-MKE -
Vin
1HD1BVJ13NB023737 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
2477 -
Color
BLACK -
Family
Cruiser
2022 Harley-Davidson® Softail® Standard Raw, stripped-down bobber style. A blank canvas for customization. Features may include: THIS IS THE RIGHT BIKE FOR Artists and customizers in love with the old-school look City cruising or light touring with a low-slung stance MIlwaukee-Eight® 107 V-Twin engine and easy-reach bars MILWAUKEE-EIGHT© 107 ENGIN...
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$153Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2021 Harley-Davidson® FLHCS - Heritage Classic 114
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U024814-MKE -
Vin
1HD1YBK18MB024814 -
Vehicle Type
Motorcycle / Scooter -
Category
Softail -
Odometer
34297 -
Color
Black Jack Metallic -
Family
Cruiser
2021 Harley-Davidson® Heritage Classic 114 The quintessential American cruiser. Showstopping vintage details and pure rock and roll style. Features May Include THIS IS THE RIGHT BIKE FOR Riders ready to chase excitement across state lines Highway riding with full fenders and detachable windscreen Milwaukee-Eight® 107 or 114 V-Twin engine and steel...
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$183Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2021 Harley-Davidson® FLHR - Road King®
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U652497-MKE -
Vin
1HD1FBC10MB652497 -
Vehicle Type
Motorcycle / Scooter -
Category
Touring -
Odometer
17086 -
Color
Midnight Crimsion with Stone Wash White Pearl -
Family
Grand American Touring
2021 Harley-Davidson® Road King® A stripped-down highway legend with classic chrome styling and modern touring performance. Features may include: THIS IS THE RIGHT BIKE FOR Riders looking to burn through miles with authority Neo-classic style with Hiawatha headlamp and nacelle Milwaukee-Eight® 107 V-Twin engine and one-touch saddlebags Milwaukee-E...
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$213Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2021 Harley-Davidson® FLHTK - Ultra Limited
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U625141-MKE -
Vin
1HD1KEF11MB625141 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
39657 -
Color
Black -
Family
Grand American Touring
2021 Harley-Davidson® Ultra Limited Premium touring performance with zero compromises to the ride. Features may include: THIS IS THE RIGHT BIKE FOR Riders seeking the fully-loaded touring experience Bold styling and comfort with a vented batwing fairing Twin-Cooled™ Milwaukee-Eight® 114 engine and heated grips Milwaukee-Eight® 114 Engine The most ...
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$213Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2021 Harley-Davidson® FLHXS - Street Glide® Special
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U640453-MKE -
Vin
1HD1KRP1XMB640453 -
Vehicle Type
Motorcycle / Scooter -
Category
Touring -
Odometer
42694 -
Color
Billiard Red -
Family
Grand American Touring
2021 Harley-Davidson® Street Glide® Special A factory-custom bagger with highway-shredding power, in a blacked-out or chrome finish. Features May Include THIS IS THE RIGHT BIKE FOR Milwaukee-Eight® 114 V-Twin engine and Prodigy™ wheels Never before offered two-tone paint schemes Bright white Daymaker® LED headlamp Milwaukee-Eight® 114 Engine The m...
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$213Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2021 Harley-Davidson® FLHXS - Street Glide® Special
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U618251-MKE -
Vin
1HD1KRP19MB618251 -
Vehicle Type
Motorcycle / Scooter -
Category
Touring -
Odometer
42193 -
Color
Billiard Red -
Family
Grand American Touring
2021 Harley-Davidson® Street Glide® Special A factory-custom bagger with highway-shredding power, in a blacked-out or chrome finish. Features May Include THIS IS THE RIGHT BIKE FOR Milwaukee-Eight® 114 V-Twin engine and Prodigy™ wheels Never before offered two-tone paint schemes Bright white Daymaker® LED headlamp Milwaukee-Eight® 114 Engine The m...
Read More -
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$131Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2021 Harley-Davidson® FXST - Softail® Standard
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U015338-MKE -
Vin
1HD1BVJ16MB015338 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
4537 -
Color
Vivid Black -
Family
Cruiser
2021 Harley-Davidson® Softail® Standard Raw, stripped-down bobber style. A blank canvas for customization. Features may include: THIS IS THE RIGHT BIKE FOR Artists and customizers in love with the old-school look City cruising or light touring with a low-slung stance MIlwaukee-Eight® 107 V-Twin engine and easy-reach bars MILWAUKEE-EIGHT® 107 ENGIN...
Read More -
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$183Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2021 Harley-Davidson® Pan America™ 1250 Special
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U305175-MKE -
Vin
1HD1ZES15MB305175 -
Vehicle Type
Motorcycle / Scooter -
Category
Adventure -
Odometer
3397 -
Color
ORANGE/WHITE -
Family
Adventure Touring
2021 Harley-Davidson® Pan America™ 1250 Special The Pan America™ 1250 Special motorcycle is our premier two-wheel multi-tool built to endure, designed to explore, and engineered for adventure. Enthusiasts who require top-of-the-line comfort and performance For riders who see touring as detouring – on road and off Riders looking for power, tech, an...
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$154Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2021 Harley-Davidson® RH1250S - Sportster® S
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U312075-MKE -
Vin
1HD1ZC411MB312075 -
Vehicle Type
Motorcycle / Scooter -
Category
Sport -
Odometer
3623 -
Color
BLACK -
Family
Sport
2021 Harley-Davidson® Sportster® S Sportster® S is the first chapter of a whole new book of the Sportster saga. A legacy born in 1957 that outperformed the competition is now rebuilt to blow away the standards of today. Features may include: THIS IS THE RIGHT BIKE FOR Riders who desire top-of-the-line performance and stunning style Aggressive ridi...
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$198Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
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$124Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2020 Harley-Davidson® FXLR - Softail® Low Rider®
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U014985-MKE -
Vin
1HD1YNJ15LB014985 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
30182 -
Color
Billiard Red -
Family
Softail®
2020 Harley-Davidson® Softail® Low Rider® RUGGED INDIVIDUALISM TURNED TO METAL With styling reminiscent of the original in the ’70s, the tradition of individualism carries on in the powerful Low Rider® motorcycle. Features may include: Throwback Style Dual tank mounted gauges, headlight visor and ’70s-inspired tank graphics carry forward the tradi...
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$192Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
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$168Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2019 Harley-Davidson® FLHTK - Ultra Limited
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U616210-MKE -
Vin
1HD1KEF18KB616210 -
Vehicle Type
Motorcycle / Scooter -
Category
Touring -
Odometer
56640 -
Color
INDUSTRIAL GRAY/BLACK DENIM -
Family
Touring
2019 Harley-Davidson® Ultra Limited EXPERIENCE A RIDE THAT IS ANYTHING BUT STANDARD It’s loaded. From the new Milwaukee-Eight® 114 engine to the heated hand grips. Classic Batwing fairing, all new BOOM!™ GTS infotainment system, and plenty more. Yes, you can have it all. Features may include: FOR RIDERS WHO WANT IT ALL MILWAUKEE-EIGHT® 114 ENGINE ...
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$198Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2018 Harley-Davidson® FLDE - Softail® Deluxe
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
u063692-MKE -
Vin
1HD1YCJ1XJC063692 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
38912 -
Color
BLACK -
Family
Softail®
2018 Harley-Davidson® Softail® Deluxe Show-stopping, old-school glam, Deluxe is a nostalgic boulevard custom that turns heads. Features may include: Pull-Back Handlebars These bars offer confidence-inspiring easy-reach ergonomics, with a chrome pullback riser that gets the grip even closer and gives the front end a dynamic aerodynamic contour. Chr...
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$183Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2018 Harley-Davidson® FLFBS - Softail® Fat Boy® 114
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U081350-MKE -
Vin
1HD1YGK19JC081350 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
9099 -
Color
Industrial Grey -
Family
Softail®
2018 Harley-Davidson® Softail® Fat Boy® 114 The original fat custom icon that changed it all has done it again. Satin chrome finishes. Beefy 240mm rear tire. And now available in a Milwaukee-Eight® 107 or 114 Big Twin Engine for the most muscular, unstoppable Fat Boy® motorcycle ever. Features may include: Satin Chrome Finishes An all-you-can eat ...
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$168Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2018 Harley-Davidson® FLHTCU - Electra Glide® Ultra Classic®
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U612452-MKE -
Vin
1HD1FCC17JB612452 -
Vehicle Type
Motorcycle / Scooter -
Category
Touring -
Odometer
55893 -
Color
TWISTED CHERRY/SILVER FORTUNE -
Family
Touring
2018 Harley-Davidson® Electra Glide® Ultra Classic® Since 1965, the ELECTRA GLIDE® model has been the choice of riders who want the essential touring machine. One ride and you’ll know why. Features may include: Milwaukee-Eight® V-Twin Engine A powerful, smooth-running engine with crisp throttle response and a pure, soul-satisfying rumble. Responsi...
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$198Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2018 Harley-Davidson® FLSL - Softail® Softail Slim®
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
CON058307-MKE -
Vin
1HD1YDJ13JC058307 -
Vehicle Type
Motorcycle / Scooter -
Category
Cruiser -
Odometer
3283 -
Color
Red, White & Blue -
Family
Softail®
2018 Harley-Davidson® Softail Slim® A raw, vintage H-D style, with a modern edge. The all-new Softail Slim® motorcycle is 35 pounds lighter than last year’s model, with more power, more lean angle, and a redesigned suspension. Features may include: Dark Polished Finishes Features blacked-out metal from the Hollywood handlebars to the black steel l...
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$302Per Month
Plus Tax.72 Months. 9.99% APR. 20% Down Payment.
Quick Look 2017 Harley-Davidson® FLHXSE - CVO™ Street Glide®
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Condition
Pre-owned -
Location
Milwaukee Harley-Davidson -
Stock Number
U952924-MKE -
Vin
1HD1PXF19HB952924 -
Vehicle Type
Motorcycle / Scooter -
Category
Touring -
Odometer
28828 -
Color
ORANGE/BLACK -
Family
CVO™
2017 Harley-Davidson® CVO™ Street Glide® This is the hot rod bagger decked out fender to fender with custom details, mind-blowing paint and enough Premium BOOM!™ Audio to throw your own street party at Bike Week. Everything you thought could never roll out of a factory. The CVO Street Glide® is decked out fender to fender with custom details and o...
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