This month's Chicago Magazine has a feature this month on where to find vintage everything in the city--including clothes and accessories. Among the listings: Pilsen's Knee Deep Vintage, which should be your first stop if you're looking for secondhand boots, and Lulu's at the Belle Kay, a great spot for bags. Mentioned as a good place to find antique wedding bands and engagement rings is Oak Park's the Gold Hatpin.
Here are a few tips of my own:
Several weeks ago I attended a vintage shopping party where I coveted a Claude Montana burgundy fur-collar jacket and couldn't resist a long, silk gown from the 30s (when I'll have an occasion to wear it I have no idea) from Saffron Vintage.
And then there's vintage clothing dealer Evelyn Daitchman, who hosts private shopping parties in a loft off Lake Street--everything from old costumes from the Lyric Opera to a fabulous patterned trench that looked like it could have inspired Miuccia Prada a few seasons ago. But you have to be invited.
If you're more focused on deals--whether they're on stuff that's new or used--Chicago's Ultimate Bargain Shopping Guide is still online.