5490 Park Place Rosemont, IL 60018 847.454.7244 Powered By Windy City Motorcycle Company Chicago Harley-Davidson® Harley-Davidson® Motorcycles For Sale in Chicago, IL Browse All Motorcycles New Used Browse Harley Motorcycles Street Sportster Dyna V-Rod Softail Touring Trike CVO Electric Refine Search Reset ACTIVE FILTERS1 Price Clear All $1 - $33k LOCATION Barbed Wire HD Chicago HD Wrigleyville Fox River HD Illinois HD Lakeshore HD Milwaukee HD Starved Rock HD West Bend HD Wild Fire HD Windy City International Cycle Woodstock HD Woodstock KTM/Triumph CONDITION New Pre-owned YEAR Minimum Year Min 1975 1984 1985 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 Maximum Year Max 1975 1984 1985 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 MAKE PRICE $1 $33k VEHICLE TYPE CATEGORY FAMILY ODOMETER Don't see what you're looking for? Chicago Harley-Davidson® Inventory Search Inventory Sort Results Sort By Vehicle Type (A to Z) Vehicle Type (Z to A) Inventory Most Recent Make (A to Z) Make (Z to A) Mileage (Low to High) Mileage (High to Low) Model (A to Z) Model (Z to A) Est. Monthly Payment (Low to High) Est. Monthly Payment (High to Low) Price (Low to High) Price (High to Low) Category (A to Z) Category (Z to A) Year (Old to New) Year (New to Old) How Many Results Per Page Show 10 Show 20 Show 30 Show 40 Show 50 Page 1 of 71 VIEW Showing 1-20 of 1417 results 16 2022 Indian Motorcycle® FTR 1200 S Share Our Price $14,995 Get Financing $228PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 17 2022 Kawasaki KL650GNFNL Share Our Price $7,499 Get Financing $117PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle REDUCED PRICE 17 2021 BMW R 18 Classic First Edition Share Retail Price $17,999 Our Price $15,499 Savings $2,500 Get Financing $235PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle REDUCED PRICE 16 2021 BMW R 18 First Edition Share Retail Price $15,999 Our Price $13,999 Savings $2,000 Get Financing $213PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 16 2021 Can-Am® SPYDER F3 Share Our Price $21,995 Get Financing $331PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle FINANCING AVAILABLE !! 2021 Can-Am® Spyder® F3-S Special Series SE6 Share Our Price $20,995 Get Financing $317PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 16 2021 Ducati Streetfighter V4 S Ducati Red Share Our Price $23,994 Get Financing $361PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 17 2021 Harley-Davidson® FLFBS - Fat Boy® 114 Share Our Price $20,399 Get Financing $308PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 2 2021 Harley-Davidson® FLFBS - Fat Boy® 114 Share Our Price $20,399 Get Financing $308PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 17 2021 Harley-Davidson® FLH - Electra Glide® Revival™ Share Our Price $32,990 Get Financing $494PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 5 2021 Harley-Davidson® FLHCS - Heritage Classic 114 Share Our Price $20,990 Get Financing $317PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 17 2021 Harley-Davidson® FLHCS - Heritage Classic 114 Share Our Price $20,999 Get Financing $317PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 2021 Harley-Davidson® FLHR - Road King® Share Our Price $20,299 Get Financing $306PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 2021 Harley-Davidson® FLHR - Road King® Share Our Price $19,949 Get Financing $301PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 2021 Harley-Davidson® FLHR - Road King® Share Our Price $19,949 Get Financing $301PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 2021 Harley-Davidson® FLHRXS - Road King® Special Share Our Price $23,449 Get Financing $353PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 17 2021 Harley-Davidson® FLHRXS - Road King® Special Share Our Price $24,390 Get Financing $367PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 2021 Harley-Davidson® FLHTK - Ultra Limited Share Our Price $32,194 Get Financing $483PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle 17 2021 Harley-Davidson® FLHTK - Ultra Limited Share Our Price $31,199 Get Financing $468PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle PRE-SURCHARGE PRICE 17 2021 Harley-Davidson® FLHTK - Ultra Limited Share Our Price $31,189 Get Financing $468PER MONTH Plus Tax.72 Months. 9.99% APR. 20% Down Payment. View Disclaimer GET A QUOTE DETAILS CONTACT US Toggle more information for this vehicle Page 1 of 71 INFO 5490 Park Place Rosemont, IL 60018 847.454.7244 "Powered by Windy City Motorcycle Company with 15 locations across Chicagoland and Southern Wisconsin." 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