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Chicago’s Oldest Gay Bars Have Stories to Tell

As the world recognizes the 50th anniversary of Stonewall, we sent photographers to three of the city’s oldest gay bars — one on the South Side, one on the North Side, and one right in between.

Photo: (above) Pat Nabong
Jeffery Pub
Photo: Max Herman

For Black, Gay Chicagoans, It’s Always Been Jeffery Pub

In the first installment of our series on the city’s oldest gay bars, we visit the South Shore stalwart — Chicago’s only black-owned establishment of its kind.


Little Jim’s Tavern
Photo: Pat Nabong

Little Jim’s Tavern Is Big on History

Forty-five years on, the Boystown mainstay is an intergenerational mosaic of Chicago’s gay community.


Second Story
Photo: Pat Nabong

Second Story Honors Streeterville’s Queer Past

Closing out our historical gay bar series is this under-the-radar downtown hideaway, which has provided a refuge for locals and tourists alike for 35 years.



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