Lincoln Park, Wicker Park, and Bucktown

Today, Lincoln Park epitomizes all the things that people love to hate about yuppified urban areas: stratospheric housing prices, teeny boutiques with big-attitude salespeople, and plenty of fancy-schmancy coffee shops, wine bars, and cafés. That said, it's also got some of the prettiest residential streets in the city, that gorgeous park, a great nature museum, a thriving arts scene, and the famous Steppenwolf Theatre.

Old Town, bordered by Division Street, Armitage Avenue, Clark Street, and Larrabee Street, began in the 1850s as a modest German working-class neighborhood. Now its diverse population resides in some of the oldest—and most expensive—real estate in Chicago. Its most renowned tenants are the comedy clubs The Second City and Zanies.

Bucktown, which surrounds Milwaukee Avenue north of North Avenue, got its name from the goats kept by the area's original Polish and German immigrants. Wicker Park, the area south of North Avenue to Division Street, is now inhabited by creative types, young families, thirtysomething professionals, and university students. Cutting-edge galleries, coffeehouses, nightclubs and funky shops line its streets—a far cry from the Mag Mile. Farther south is Ukrainian Village. Artists are now encroaching, but evidence of ethnic roots remains strong in this neighborhood.