True to its name, the street, which began as a Native American trail, eventually leads north to the state of Wisconsin and through Kenosha and Racine towards Milwaukee, though not directly. Starting with a short section at N. Canal and W. Lake Streets, it begins in earnest at the corner of N Desplaines and W. Kinzie Streets and heads northwest for about before joining Skokie Highway in Gurnee, Illinois, which eventually merges at Interstate 94 where Skokie Highway and the Tri-State Tollway split off, continuing to Milwaukee. From Harlem Avenue northwards it is Illinois Route 21. Milwaukee Avenue is a popular route for bicyclists. The southeastern end of Milwaukee Avenue is the most heavily bicycled stretch of road in Chicago, with cyclists accounting for 22% of all traffic there on a randomly selected day in September. The street is lined with storefronts, restaurants and the occasional art gallery through most of the city. The CTA's Blue Line runs beneath or alongside Milwaukee Avenue from its beginning at Canal and Lake Streets out to Logan Boulevard, with stations at Grand Avenue, Chicago Avenue, Division Street, Damen Avenue, Western Avenue, California Avenue and Logan Square. The Kennedy Expressway roughly parallels Milwaukee Avenue as well. Just north of Armitage it passes the Chicago LandmarkCongress Theater and at Addison Street it passes the Chicago Landmark Schurz High School. Past Irving Park Road it turns more northerly and the Blue Line crosses again at the Jefferson Park station passing the Gateway Theatre. It exits the city at about Albion Avenue and enters Niles, Illinois.. At Golf Road it passes the Golf Mill Shopping Center. It crosses the Des Plaines River just south of the Chicago Executive Airport, formerly known as Palwaukee Municipal Airport. From thence it roughly follows the Des Plaines River north, passing through such communities as Wheeling, Lincolnshire, Vernon Hills, and Libertyville, where it forms the historic core of Libertyville's downtown area. It continues on past Gurnee before merging with the Skokie Highway near Wadsworth.
Milwaukee Avenue runs through the commercial heart of Chicago's vibrant and trendy Wicker Park and Bucktown neighborhoods. The Double Door theater and Irazu Costa Rica Restaurant front the avenue in this section. On an episode of Food Network's Diners, Drive-ins and Dives, host Guy Fieri walks from the Milwaukee Avenue pavement to Irazu's outdoor patio to sample the food for the TV audience. Sections of the movie High Fidelity were filmed in buildings along Milwaukee Avenue, including the Double Door and the fictional record store that is the nexus of the character's lives. Although the movie Wicker Park was filmed in Canada, the story is set in this area of Wicker Park, Chicago. The busy six corner intersection of Damen Avenue, North Avenue, and Milwaukee is the center of the "24 hour" Wicker Park scene with dozens of bars and restaurants, making for popular nightlife. The Flat Iron Arts Center, built in 1913 and designed by Holabird & Roche, is sited at this intersection. In 2015, the Spike Lee movie Chiraq was being filmed in Chicago, with a scene including rapper actor Nick Cannon filmed at the Double Door on Milwaukee Avenue. The movie palace Congress Theater, a designed Chicago landmark built in 1926, is located at 2135 N. Milwaukee.
Logan Square
Just northwest of Bucktown, Milwaukee Avenue traverses the heart of Logan Square, Chicago, a gentrifying neighborhood. Milwaukee Avenue runs on a diagonal through the parkway of the boulevards, Logan Boulevard and Kedzie Avenue at a traffic circle surrounding the Illinois Centennial Monument.
