4 Best Sights in Chicago, Illinois

Michigan Avenue, or Mag Mile as some call it, is a potpourri of historic buildings, upscale boutiques, department stores, and posh hotels. (It is also the city's most popular place for people-watching.) Among its jewels are the Tribune Tower, the Wrigley Building, 875 North Michigan Avenue (formerly the John Hancock Center), the Drake Hotel, and the Historic Water Tower.

Serving as the border that separates Wicker Park from Ukrainian Village to its south, Division Street has become a shopping and dining destination in its own right. Bars, boutiques, and trendy restaurants line the once-gritty thoroughfare, which lent its name to journalist Studs Terkel's 1967 book about urban life. To start your exploration, head west on the stretch of Division between Ashland and Leavitt avenues.

A bustling center for food processing and distribution as recently as the 2000s, this former industrial district transformed into an upscale stretch of gleaming corporate offices, luxury condos, and Michelin-star restaurants with remarkable speed. The last of the seafood, produce, and meatpacking plants were gone by the end of the 2010s; Fulton Market is now a full-on dining and nightlife destination.

The Southport Corridor, as this stretch of pavement is known, is lined with independent shops and high-end boutique chains to serve the area's well-dressed urban professionals with money to burn. Those stores are peppered amongst neighborhood pizza joints and classic taverns, bookended by music venue Schubas Tavern to the south and the historic independent movie theater The Music Box at the north.