A journalist comes to Chicago to profile a woman attending her 500th Bears game — then falls in love with the football fanatic’s grandson.
This is the premise of Hallmark’s “Holiday Touchdown: A Bears Love Story.” The film, which features cameos from Caleb Williams, Ben Johnson, and more, premiered earlier this month. Over the weekend, another new Chicago romance dropped: “Love Language,” in which Chloë Grace Moretz stars as an addled wedding vow writer.
While I’m not sure I’d call the Hallmark flick a rom-com (just watch the trailer), it’s fun to see our city as a romantic backdrop again. Throughout the ‘90s, Chicago was the setting for a certified banger run of rom-coms. Let’s take a trip down memory lane — or, over the river downtown, like a frazzled, windswept heroine.
‘While You Were Sleeping’ (1995)
Only Sandra Bullock could not make this premise not insanely creepy: A forlorn CTA fare token collector ingratiates herself into the family of a handsome rider while he’s unconscious in the hospital after an accident on the tracks.
‘My Best Friend’s Wedding’ (1997)
Look, we all agree Julia Roberts’ character is in the wrong. She spends the entire movie trying to break up two people who genuinely love each other. But I DON’T CARE. Give me the architectural boat waltz! Give me the full-restaurant Dionne Warwick rendition!
‘Love Jones’ (1997)
Less conventional than other ‘90s rom-coms, “Love Jones” is (famously) bittersweet. It also takes inspiration from Chicago’s underground poetry scene at that time. Nia Long stars as a photographer who crosses paths with a writer (Darius Lovehall) at a spoken-word club.
‘Return to Me’ (2000)
I recommend this gem every chance I get — most recently on World Gorilla Day. The premise is ridiculous: “Grace has Bob’s dead wife’s heart!” But it works, thanks to Minnie Driver’s earnest performance. It’s also Chicago angel Bonnie Hunt’s directorial debut.
Later (Offbeat) Additions
These aren’t quite romantic classics but feature some unique shots of the city.
- “Stranger Than Fiction” (2006) is a postmodern rom-com in which Will Ferrell’s character falls for a baker (Maggie Gyllenhaal). Catedral Cafe (today La Catedral) in Little Village stood in as the bakery.
- “The Vow” (2012) is not a good movie — but it features my all-time favorite wedding scene. Rachel McAdams and Channing Tatum’s characters wed guerrilla-style in the Art Institute and kiss under the Bean, McAdams flouncing in a short, rosy-pink dress.
- “Drinking Buddies” (2013) is an extra mumbly mumblecore, starring Olivia Wilde and (Chicagoland’s own) Jake Johnson as Revolution Brewery employees. If you like “Drinking Buddies,” you might like the director's Chicago-set Netflix series “Easy.”
- “I Used to Go Here” (2020) mostly takes place in Carbondale. It’s also not technically a romance, unless you count falling in love with life again. But as a struggling writer from Lincoln Square, Gillian Jacobs checks the rom-com boxes.
