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Exploring Chicago’s Randolph Street Market: A treasure trove of vintage finds

May 21, 2025
2016 05 27 18.52.27

You know it’s festival season when you start to see Randolph Street Market open and all the lovely vintage finds start calling your name. The market opens opens this weekend, with one festival in the city, then is back in September.

  • May 24-25 – Randolph Street Market, 1341 W Randolph St, Chicago
    There’s entertainment all day, and a huge line-up of food including J Spice (Carribbean), Happy Lobster, Mr Greek, Blazed Bakery, Maggie’s Sweets and more. Also, 3 bars!
  • September 13-14 – Highland Park Vintage Shindig, Highland Park Community House, 1991 Sheridan Rd, Highland Park
  • September 27-28 – Randolph Street Market, 1341 W Randolph St, Chicago
  • October 5 – Modern Vintage Chicago, Ravenswood Event Center, 4025 N Ravenswood Ave, Chicago
  • November 15-16 – Holiday Market, Plumbers Hall, 1340 W Washington, Chicago
  • December 13-14 – Holiday Market, Plumbers Hall, 1340 W Washington, Chicago

Here are some finds from my sneak peek (and if you get the lion head, you must show it on display!):

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Guilty Pleasures Coctktail Cupcakes
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2016 05 27 18.20.58