10 Great Neighborhoods in Chicago

From River North to the Gold Coast, to Wicker Park and the South Loop, discover some of Chicago's best neighborhoods and find out which one is right for you.

Photo via Coldwell Banker Real Estate Probably the most famous photo-op spot in the Gold Coast, or all of Chicago. The Oak Street Beach gets bodies tanning and runners and bikers hitting a stretch of the nearly 19-mile Lakeshore Trail. Rents are steep but property values remain constant in this wealthy enclave. At one point, the Gold Coast had the highest reported income in the country.

Gold  Coast/Old Town

Boundaries: Between North Avenue south to Chicago Avenue, from LaSalle Avenue east to Lake Michigan

Old money and stunning lake views characterize this hot neighborhood that runs contrary to the Chicago phrase: “cooler by the lake.” Oprah once lived on the border of this high-priced community, where homebuyers can pay millions for a two-bedroom condo. And if you're into "intentional living," or sharing humongous spaces commune style, this area has some of Chicago's largest old homes that could fit the bill. “People are drawn to this area because of the nightspots, the good food, its proximity to the lake and to the business district,” says Prudential Preferred Properties Realtor Carla Walker.

The main commercial center for this neighborhood is Oak Street, the Rodeo Drive of the Midwest. Hermes, Versace and Gucci clothing stores mingle with four-and five-star restaurants offering outdoor seating in the summer. Oak Street runs right through the heart of an area known as the “Viagra Triangle.” This slice of the city, bounded by Rush Street, State Street and Chicago Avenue is nicknamed for the affluent, white-haired men that can be seen courting well-dressed women in their 20s at area singles bars. Coincidentally, Hugh Hefner’s original playboy mansion, at 1340 N. State St., is just down the street from the Viagra Triangle.

During summer, Rush Street Concerts at the landmark St. James Cathedral showcase live performances for an hour. 

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