Wicker Park & Bucktown: Chicago

Over the past ten years, Bucktown and Wicker Park have blossomed into the neighborhoods for Chicago's twentysomethings to call home. Bars, restaurants and vintage stores all dot the streets surrounding what's known as the "Six Corners:" the lively intersection of Milwaukee, North and Damen Avenues. Side streets are lined with quaint walk-up apartment buildings where the rent has been steadily rising.

This section of the city is home to two of Chicago's hippest music venues: Subterranean Lounge and Double Door. If you visit in the summer, you may be able to catch some of the best music outside at Green Music Fest and Wicker Park Fest.

All that rocking and rolling can help guests work up quite the appetite, and there is no shortage of opportunities to sample some of Chicago's best flavors here. If you're looking to hang with the locals, head to Big Star where you'll enjoy one of the finest tacos you'll ever have north of the border. For a more relaxed evening and a much shorter wait, try Bin Wine Cafe.