Wicker Park, IL, Website

Wicker Park, Illinois. In Wicker Park, art and commerce peaceably co-exist, with the occasional hiss or growl. Its streets have become the literal fine lines between kitsch and art; dives and faux dives; cheap and elite eats, resale and trendy new.

Despite its gentrifying residential area and the encroachment of high-ticket venues, there is an attempt to maintain the eclectic, artistic and often downright oddball environment. The result is a mix of cool, wannabe cool and couldn't-care-less-about-cool (hence, really cool) stops. Select from a variety of hipper-than-thou bars and restaurants, or hunt out the cheap eats and worthy destinations (like the Double Door, a one-time Rolling Stones pit stop).

The intersection of Damen, Milwaukee and North avenues ("ground zero") is where much of the commercial boom has resonated. A trip down Milwaukee these days is like running past one of those rotating Hanna Barbera cartoon backgrounds (rock-cactus-rock-cactus-rock), only with chi-chi restaurants alternating with fearfully hip boutiques.

Most of the gallery action (like Ten In One Gallery on Damen and Beret International on Milwaukee) is here, anchored by the Around the Coyote art show each September. But there's more to Wicker Park these days. Other eclectic business strips run along the border or cut a swath through residential sections. Division Street now boasts the likes of Liquid Kitty. If you're too unhip for that room, there's the far more comfy Gold Star Bar (fighting the faux dive label ever since Joan Cusack started hanging out there). Browsing fun includes Myopic Books, and Specimen Products, a guitar store next door.

Remnants of the old neighborhood can be found on the border streets: Ashland Avenue, Western Avenue and Division Street. There's some down-and-dirty value shopping, along with a few boutiques. Results may vary—hip, kitsch, lame or geek chic—but chances are it'll be just the thing for walking the line in Wicker Park.