The Loop, Including West Loop and South Loop

Internationally known landmarks like the Willis (formerly Sears) Tower, Millennium Park, and Buckingham Fountain blanket the Loop landscape and visitors and locals gush over the masterpieces at the Art Institute and the merchandise at State Street's stores. LaSalle Street, home of the thriving financial district, earned the moniker the Canyon (and the feel of one) because of the large buildings that flank either end of the relatively narrow street. The Loop oozes with Midwest friendliness, charm, and culture—it has a world-class symphony, first-class theaters, fine restaurants, and a swinging nightlife.

For an especially good meal, head to the West Loop. What was once Skid Row and meatpacking warehouses is now a vibrant community with trendy restaurants. Greektown, a five-block stretch of Halsted Street, serves up authentic saganaki. A thriving art scene has emerged around Fulton Market.

The South Loop's claim to fame is the Museum Campus—The Field Museum, Shedd Aquarium, and Adler Planetarium. Jutting out into the lake, it affords amazing skyline views. To the north, giant gargoyles (supposedly owls signifying wisdom) loom atop the Harold Washington Library. East on Congress at Michigan Avenue is the Romanesque Revival-style Auditorium Building designed by architects Sullivan and Adler.