Milwaukee Ave offers a trove of hip vintage fashion, book and record shops. Damen Ave's shops are a bit more upscale, with perfume, children's clothing and artisanal gifts on offer.

Don't Miss: Vintage & Thrift Shops

The stretch of Milwaukee Ave between Division and North Aves holds the mother lode of vintage and thrift shops, with some funky shoe stores and T-shirt shops thrown in for good measure. Within a half-mile you'll pass around eight hot spots, including US #1, Una Mae's, Kokorokoko, and Ragstock. And at Buffalo Exchange, if you have some suitably fashionable threads of your own to trade in, you don't even need cash.