Except for Goose Island (undergoing development with upscale residences), the Near North Side is known for its extreme affluence, typified by the Gold Coast, Magnificent Mile, Navy Pier, and its world-famous skyscrapers. In addition, the Near North Side is the oldest part of Chicago.

Old Town is similarly upscale but promises a distinct historic charm. Victorian-style townhomes, brick buildings, and brownstone walk-ups line the residential pockets (which there are a lot of), while the busier main roads boast every convenience you could possibly need. The neighborhood's west side has all your mainstream shopping (think Whole Foods and Target), while more local haunts dominate the area as you make your way east toward the lake.

The South Side boasts a broad array of cultural and social offerings, such as professional sports teams, landmark buildings, museums, educational institutions, medical institutions, beaches, and major parts of Chicago's parks system.

The West Side is of historical and cultural significance to Chicago, partly because of its historic purpose as a gateway for immigrants and poorer residents to settle away from the wealthier lakeside and central business districts.