Take a stroll down Milwaukee Avenue, arguably the most intriguing of Chicago's crooked streets.
A cool shop stocked with both new and vintage gear for both genders. Affordable to boot!
Buy, sell, or trade both vintage and thrift (and housewares, if you're so inclined). This place is downright awesome.
You won't see footwear clones all over the sidewalk when you're sporting kicks from here. Hard-to-find styles and brands populate the shelves.
Charmingly minuscule bar w/ gigantic, STRONG cocktails! The marg is famous, the gimlet should be & the Old Fashioned is brandy-soaked bliss.
My favorite "slashie" in the city! On the bar side, live tunes and no-nonsense bartenders. On the liquor store front, there's a seriously comprehensive craft beer selection.
Homemade soaps, other lovely smelly things, and cute baubles always suck me in when I'm in the area.
Reproductions, reprints, and original works in an unintimidating setting. Most of the art is created by the owner, but others' work gets some play too. Aficionados and curious Wicker Parkers harmoniously peruse the walls.
Sprawling, comfy work space perfect for laptoppers. Cool artwork & artsy vibe. Serious espresso bevs, pastries & lots of vegan options.
A local, super-friendly wine shop. Stop by for a tasting event on Saturday.
A legit Irish deli and grocer with the world's sweetest owner. Try the chicken soup and corned beef sandwich. And FYI: a half sandwich is the size of a full. Bonus.
Great for an afternoon with the laptop, but even greater for a night with a latte (or a brew or spiked coffee bev, if you're so inclined). Live tunes at night too!
I love having this place in the 'hood. The crew is nice (and accommodating) as can be, and the selection is always changing. Great sandwiches too.