Lincoln Park

Today Lincoln Park epitomizes all the things that people love—and 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. 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 renowned Steppenwolf Theatre.

Old Town, bordered by Division Street, Armitage Avenue, Clark Street, and Halsted 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 best-known tenants are the Second City and Zanies comedy clubs.