Neighborhood Guides

Get to Know These Romantic Spots

Posted on February 8, 2023 | Updated on September 30, 2025

Sidney Madden

O'Hare Airport

Transportation Secretary Pete Buttigieg proposed to his husband Chasten at O’Hare. (Chris Rycroft / Wikimedia Commons)

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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