The Oriental Theater
24 W. Randolph St.
Back in the height of the Jazz Era, the Oriental Theater was among the most popular movie theaters in the city. Throughout the 70s and 80s, the Oriental showed exploitation films that respectable theaters refused to show.
The theater closed to the public until the 1990s when a Canadian company restored the theater. The Oriental’s 2009 production of Wicked was the longest-running Broadway-touring play in Chicago’s history.
State/Lake El stop: Walk two blocks south on State Street. Turn right on Randolph Street.
Portage Theater
4050 N. Milwaukee Ave.
The Portage Theater is home to the Silent Film Society of Chicago, but their screenings range from “B-Movie Madness” to the 1958 War of the Colossal Beast. The theater tends toward marathons of similarly-themed movies, generally not the sort of films you’d catch in the local AMC. The theater’s quirky atmosphere features a full pipe organ.
Take the Brown line to the Irving Park stop. Get on Bus X80 towards Harlem. Get off at Cicero.
The Music Box Theater
3733 N. Southport Ave.
This is the place for independent film in Chicago. From 1977 to 1983, it played Spanish films and porn. The theater began playing old films in 1983, and independent, cult and foreign-language films were added to the roster soon thereafter.
Ride the Red Line to the Addison stop. Walk five blocks west to Southport Ave, turn right, and walk two blocks north.
Sunset Cinema: It’s a bike-in!
2728 W. Evergreen Ave.
Sunset Cinema dedicates itself primarily to cult classics of late 80s and early 90s, films that 25-year-old founder Alex Gvojic describes as “the cult classics for people my age.” Unfortunately, the Sunset Cinema is only in operation during Spring and Summer. But at least you can look forward to Pee Wee’s Big Adventure when the snow melts away.
Bring your bike on the Red Line, get off at Clark and Division, and take Bus 70 towards Austin. Get off at Division and Washtenaw. Bike four blocks north to 2728 W Evergreen Ave.