Airbnb? I'd say Wicker Park, Logan Square, Uptown or East Rogers Park. Wicker and Logan Square are more hipster. Uptown and Rogers Park are a bit more hood, but not necessarily ghetto.

Art of Pizza is a cool spot. Pizano's on State Street is cool. Of course there's the tourist spots like Gino's East and Giordano's. And Lou Malnati's. L'Patron is a good spot for tacos and such.

Emporium is cool, if you like video games and/or beers. Dusty Groove is good for buying music and vinyl. The Wild Hare and The Promontory are cool music venues, but on opposite sides of town.

Walking Michigan Avenue in the wintertime is pretty dope. The Water Tower, Nordstrom, the Apple Store, it all looks so dope at night.