A good way to explore many of Chicago’s 77 neighborhoods in one fell swoop is to venture along Western Avenue. It used to mark the western edge of the city, and at 24 miles, it’s an exceedingly long street — running from Howard Street on the north to 119th Street on the south — so there’s plenty to see. We’ve picked some of our favorite attractions along the way, including Margie’s Candies, Rosehill Cemetery (the final resting place of Oscar Mayer, Richard Sears, and Montgomery Ward), and the Empty Bottle.
1035 N. Western Ave. Ukrainian Village
A man lights a cigarette outside the Empty Bottle tavern and music venue.
9900 S. Western Ave., Beverly
Janson’s Drive-In, which opened in 1960, is known for fresh banana milkshakes and Angus burgers.
1960 N. Western Ave., Logan Square
Margie’s Candies’ neon sign has been beckoning Chicagoans since 1921, when Peter George Poulos opened his ice cream parlor at Western and Armitage Avenues.
1837 S. Western Ave., Heart of Chicago
The 24-hour diner Don’s Grill serves up cheeseburgers and ham off the bone.
3417 N. Western Ave., Roscoe Village
A man carries balloons out of Party City.
Western and Bryn Mawr Avenues, Lincoln Square
Rosehill Cemetery, founded in 1859, is one of the city’s most historic graveyards. The Joliet-limestone entrance gate was designed by Chicago Water Tower architect William W. Boyington, who is buried in Rosehill.
3333 N. Western Ave., Roscoe Village
Economy Auto Mart is one of the dozens of car dealers that line Western Avenue.