Valentine’s Day movie screenings in Chicago

Get off the couch and make a Valentine’s date to see these classic romances on the big screen

Photograph: courtesy 20th Century FoxAn Affair to Remember

Stuck on what to do with your significant other for Valentine’s Day? You could take them to one of the city’s most romantic restaurants, or you could plan an elaborate meetup at one of Chicago’s most iconic romantic spots, all An Affair to Remember–style. Or hey, wait, you could just take them to see An Affair to Remember, or one of these other enduring romantic movies that are getting special screenings at the city's best movie theaters on and around February 14.

RECOMMENDED: Our complete guide to Valentine’s Day in Chicago

Valentine’s Day on the big screen

An Affair to Remember (1957)

A man and a woman have a romance while on a cruise from Europe to New York. Despite being engaged to other people, both agree to reunite at the top of the Empire State Building in six months. However, an unfortunate accident keeps her from the reunion, and he fears that she has married or does not love him anymore. Cary Grant and Deborah Kerr star in the classic romance, which lent its observation-deck climax to Sleepless in Seattle and a billion other pop-culture references. It's getting a TCM-branded rerelease for its 60th anniversary.

Kerasotes ShowPlace ICON. Feb 12 at 2pm; Feb 15 at 7pm. $12.50.

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When Harry Met Sally… (1989)

Too often dismissed as the bland, cutesy face of the modern romcom, the late Nora Ephron was an unacknowledged genius when it came to screenplay construction—and When Harry Met Sally remains her finest work. This is a film where everything works: Billy Crystal and Meg Ryan’s just-this-side-of-smug central couple, the gorgeous photography of New York through the changing seasons, even Harry Connick Jr.’s jazz-lite soundtrack. And it’s all rooted in that flawless script. The story is simple: Crystal and Ryan meet after college, and loathe one another on sight. As the years pass the random meetings pile up, and dislike turns to reluctant friendship. But, as the film insistently, infamously asks, can men and women ever really be just friends?

Music Box Theatre. Feb 14 at 7:30pm. $11.

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Casablanca (1942)

Rick Blaine (Humphrey Bogart), who owns a nightclub in Casablanca, discovers his old flame Ilsa (Ingrid Bergman) is in town with her husband, Victor Laszlo (Paul Henreid). Laszlo is a famed rebel, and with Germans on his tail, Ilsa knows Rick can help them get out of the country. The Music Box shows the Best Picture Oscar winner in 35mm; the screening is preceded by a Valentine’s Day sing-along of old-timey love songs.

Music Box Theatre. Feb 12 at 2:00pm. $12.

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William Shakespeare's Romeo + Juliet (1996)

Baz Luhrmann’s stylized and stylish 1996 film cast the young Leonardo DiCaprio and Claire Danes as Shakespeare’s star-cross’d lovers, roaming a modern, sun– and gun-soaked Verona Beach. The ending’s still a downer, but the story’s given a highly seductive gloss—and the film features one of the best soundtracks of the ’90s.

ArcLight Chicago. Feb 21 at 7:15pm. $12.50.

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Moonstruck (1987)

Snap out of it! Cher, Olympia Dukakis and screenwriter John Patrick Shanley all won Oscars for this sweetly off-kilter romantic comedy in which Cher’s Brooklyn Heights widow agrees to marry a man (Danny Aiello) she doesn’t love, but then falls for his peculiar estranged brother (Nicolas Cage, still playing his crazy for comedy at this point).

Logan Theatre. Feb 14–16 at 10:30pm. $8.50.

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Singin’ in the Rain (1952)

If La La Land left you in the mood for a real classic Hollywood musical, you’re in luck. Perhaps the pinnacle of the MGM golden era of screen musicals, this infectious delight follows Gene Kelly, Debbie Reynolds and Donald O’Conner as silent-film troupers making the (finely choreographed) leap to talkies. With a script by Broadway wizards Betty Comden and Adolph Green and numbers like “Make ’Em Laugh,” “Good Morning” and the title tune featuring Kelly tap-dancing through a downpour, resistance is futile.

Logan Theatre. Feb 21–23 at 10:30pm. $8.50.

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