Softail® Motorcycles For Sale in Milwaukee & Chicago

2006 Harley-Davidson® Softail® Heritage Classic Designed to offer comfortable touring accommodations with early dresser styling, the FLSTC/I Heritage Softail® Classic features ample, 1950s-style leather saddlebags, the protection of a detachable windshield, touring handlebars and a comfortable passenger position with backrest. Laced wheels, passin...

2007 Harley-Davidson® Softail® Heritage Classic The smooth-riding enjoyment of custom touring aboard the Heritage Softail® Classic gets even better with the new Twin Cam 96B™ engine, 6-speed Cruise Drive transmission and Electronic Sequential Port Fuel Injection (ESPFI). The Heritage Softail® Classic features touring essentials like comfortable ri...

2009 Harley-Davidson® Heritage Softail® Refreshed FLSTC Heritage Softail® Classic: The Heritage Softail® Classic receives a number of other, more-subtle styling changes and new components that shift this popular model in a new, retro direction for 2009. The beefy FL front end features a front fender and chrome nacelle with clean new styling cues, ...

2008 Harley-Davidson® Heritage Softail® The Heritage Softail® Classic offers long-range touring comfort and nostalgic, dresser style with big FL front end, chrome passing lamps, studded leather saddle bags and a full windshield. A smooth ride and comfortable position carry the Heritage Softail rider far beyond the horizon. The passenger seat and t...

2006 Harley-Davidson® Softail® Deluxe FLSTN/I Softail® Deluxe combines easy-riding comfort with a heavy dose of nostalgia to create an eye-catching custom that's a joy to ride. It hugs the road on lowered suspension. The pull-back riser and handlebars and 24.5-inch seat height make the Softail® Deluxe comfortable for a wide range of riders. It's a...

2011 Harley-Davidson® Softail® Fat Boy® Lo The 2011 Harley-Davidson® Softail® Fat Boy® Lo model keeps that heritage alive more than forty years later. And this special edition shows a darker side of the original "fat custom" bike - laid-back and blacked-out with an unmistakable profile on the road.

2014 Harley-Davidson® Heritage Softail® Classic Blazing from the past with original dresser spirit and modern touring capabilities. The 2014 Harley-Davidson® Heritage Softail® Classic motorcycle FLSTC is fully equipped with modern touring capabilities and even has a removable motorcycle windshield. The Harley® Heritage Softail® Classic model featu...

2019 Harley-Davidson® Softail® Heritage Classic FROM THE SHADY SIDE OF THE FAMILY TREE The dark style, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into a new place. Features may include: TRADITION IS GOOD, BUT IT DOESN’T MEAN SITTING STILL A DARK CLASSIC WITH MODERN EDGE Dripping with gangster-era style and vint...

2008 Harley-Davidson® Softail® Fat Boy® One of the most recognizable motorcycles on the road, the FLSTF Fat Boy® defines Harley-Davidson® for many people. Still going strong after 18 years and as massive as it is iconic, the Fat Boy® rolls on a 200 mm rear tire and chopped FL rear fender. Laced leather and bullet studs trim the two-up seat and tan...

2016 Harley-Davidson® Heritage Softail® Classic Comfort as modern as this morning’s news and the power from our High Output Twin Cam 103™ engine, but the look still blazes straight from this machine’s authentic dresser past. This is too good to consign to history. The Heritage Softail® Classic drips with the nostalgia of days gone by, but that’s o...

2009 Harley-Davidson® Night Train™ Embrace darkness on the 2009 FXSTB Night Train™, with features like a blacked-out powertrain and wrinkle-black trim on the engine covers, air cleaner, oil tank, rear fender supports, drive belt sprocket and fuel tank console. The long FX front end and narrow 21-inch laced front wheel counter a beefy 200 mm rear t...

2011 Harley-Davidson® Heritage Softail® Classic The 2011 Harley-Davidson® Heritage Softail® Classic motorcycle FLSTC is fully equipped with modern touring capabilities and even has a removable motorcycle windshield. Enjoy mile after mile with a large capacity 5 gallon Softail fuel tank. The Softail tank is also dripping with authentic Harley-David...

2008 Harley-Davidson® Rocker™ C The chromed-out cousin to the Rocker™, the Rocker™ C features an industry first with the Trick seat design, which conceals a passenger pillion and struts under the solo seat cushion. To accommodate a riding partner, simply lift off the seat and the pillion folds out to deploy over the Rockertail rear section. Bril...

2019 Harley-Davidson® Softail® Heritage Classic FROM THE SHADY SIDE OF THE FAMILY TREE The dark style, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into a new place. Features may include: TRADITION IS GOOD, BUT IT DOESN’T MEAN SITTING STILL A DARK CLASSIC WITH MODERN EDGE Dripping with gangster-era style and vint...

2014 Harley-Davidson® Softail® Fat Boy® Lo Fat, dark and strong, this down-and-dirty version of the custom icon is the big dog on the road. The 2014 Harley-Davidson® Softail® Fat Boy® Lo FLSTFB model has all the features you expect on custom Harley® bike. Hearkening to the 'hardtail' choppers of the '60s and '70s, the Fat Boy Lo model is one of th...

2011 Harley-Davidson® Heritage Softail® Classic The 2011 Harley-Davidson® Heritage Softail® Classic motorcycle FLSTC is fully equipped with modern touring capabilities and even has a removable motorcycle windshield. Enjoy mile after mile with a large capacity 5 gallon Softail fuel tank. The Softail tank is also dripping with authentic Harley-David...

2011 Harley-Davidson® Heritage Softail® Classic The 2011 Harley-Davidson® Heritage Softail® Classic motorcycle FLSTC is fully equipped with modern touring capabilities and even has a removable motorcycle windshield. Enjoy mile after mile with a large capacity 5 gallon Softail fuel tank. The Softail tank is also dripping with authentic Harley-David...

2008 Harley-Davidson® Night Train™ The sinister FXSTB Night Train™ features an all-black powertrain with wrinkle-black trim on the engine covers and air cleaner, oil tank and rear fender supports, and a black fuel tank console. The raked-out FX front end and narrow 21-inch laced front wheel contrast with a meaty 200 mm rear tire on a slotted cast ...

2014 Harley-Davidson® Softail Slim® The perfect blend of classic, raw bobber style and contemporary power creates a modern ride with unmistakable old-iron attitude. The 2014 Softail Slim® FLS model blends raw, minimalistic 1940s bobber styling with up-to-date old school minimalism. The Slim model offers tons of stripped down attitude, fat features...