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Where to Finesse Vintage Finds in Chicago

Posted on May 15, 2025   |   Updated on September 30, 2025
Emily Mack

Emily Mack

Knee Deep Vintage in Pilsen.

Knee Deep Vintage in Pilsen. (Brande Jackson / Flickr)

City Cast

The Chicagoan’s Guide to Thrifting and Vintage Shopping

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I hung out so much at Belmont Army Vintage during high school, they eventually hired me. On today’s episode of City Cast Chicago, I’m spilling all about the experience ahead of the first-ever National Vintage Store Day.

That’s right, Vintage Store Day is Saturday. So here’s a guide to the places that keep Chicago looking sharp.

Belmont Army Vintage — While It Lasts

Belmont Army Vintage first opened in Lakeview in 1975. For years, it occupied the massive metallic building at 855 W. Belmont Ave., which included three floors of clothing, an army surplus, and a basement skate shop. (That’s when I worked there!) In 2018, the big store shuttered and co-owner Vivian Kim moved her vintage section a few doors down. Now, that store is set to close too.

But it’s not too late! While the current space is slated to become apartments, Kim has teased a potential relocation. There’s also a GoFundMe to save the business. In the meantime, turn out Saturday for 50% off everything there.

18th Street and Milwaukee Avenue

If, like me, you think a whole day shopping sounds like heaven, hit up Milwaukee Avenue in Wicker Park or 18th Street in Pilsen. On Milwaukee, south of the North and Damen intersection, you’ll find:

Meanwhile, on 18th street between Ashland and Racine, are four vintage gems in a row:

Other Must-Stop Shops

Real Ones Know: Village Discount Outlet

When I texted my stylish friend Kathy P. for vintage store recs, she was insulted: “You know I’m a village discount baddie.” And it’s true.

Dig hard enough at one of the city's many Village Discount Outlets, and you very well might find a true gem. Is it thrift? Is it vintage? Yes.

Apart from National Vintage Store Day, be sure to keep tabs on the Chicago Vintage Festival. Uniting over 50 vendors at a time, the events feel social and are jam-packed with different styles … but you Y2K girlies will really have a field day. The next fest is June 28 in the South Loop — don’t worry, I’ll remind you on our events page.

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