City Cast

Get to Know These Romantic Spots

Sidney Madden
Sidney Madden
Posted on February 8   |   Updated on May 27
United Airlines replying to Chasten Buttigieg's tweet with an image of Gate B5, the gate where Pete Buttigieg proposed to Chasten

Transportation Secretary Pete Buttigieg proposed to his husband Chasten at O’Hare Gate B5. (United Airlines / Twitter)

Wondering where to take your valentine? We’re sharing romantic spots that remind us where people, real and fictional, have found love and community in the city.

The Obama Kissing Rock in Hyde Park has a plaque marking where the former president and first lady smooched for the first time after some Baskin-Robbins ice cream.

O'Hare Gate B5
is where U.S. Secretary of Transportation Pete Buttigieg proposed to his now-husband.

The Art Institute is where this newsletter writer’s parents got engaged!

Hollywood Beach, Jackson Park’s Wooded Island, and the old Belmont Rocks have been meetup spots for queer Chicagoans for decades.

Leather Archives & Museum in Rogers Park has all types of history on BDSM culture, leather, kink, and fetish.Next week, we’ll share some last-minute Valentine’s Day date ideas!

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