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Best Places to Live
Chicago, Illinois
The city of big shoulders just keeps on growing, from renovated South Side to once rural outposts.
November 19, 2002: 6:25 AM EST
Joan Caplin, MONEY Magazine

NEW YORK (MONEY Magazine) - In Chicago, you've got to choose a side. And we have: the South Side. Many -- including, well, every Chicagoan north of the Loop -- will regard this as bizarre. After all, the North Side is home to some of the city's most prosperous and popular neighborhoods, such as Lincoln Park, Old Town and Lakeview. Those are great places to live, but there are precious few housing bargains left within parking distance of Wrigley Field. That's why even some once diehard North Siders have lately been moving south.

Best places to live around Chicago
South Side
Oak Park
City Stats

To be sure, much of the South Side still justifies its reputation as a hard-knock part of town, but a number of neighborhoods have been transformed almost beyond recognition. Printer's Row, just on the other side of the Loop, has seen one of its landmark buildings turned into a $230-a-night hotel, and is dotted with pricey restaurants.

In the surrounding South Loop -- where in 1991 the producers of the film "Backdraft" could safely burn down a whole building -- old factories have been rehabbed into lofts or razed to make room for townhouses. Homes here can range from $200,000 to above $400,000 but are often fitted with modern appliances and garages or off-the-street parking, which would cost a fortune up in Lincoln Park.

Even stolid, blue-collar Bridgeport -- home to five Chicago mayors -- is abuzz with new construction, attracting more price-sensitive newcomers. And Hyde Park, with its lakefront views and the gothic University of Chicago campus, has long been a South Side standout. One-bedroom condos in this eclectic, interracial enclave sell for $160,000, and $600,000 buys a large town house.

Just over Chicago's western border -- and still on the El line -- is Oak Park. In the 1970s it was one of the few Chicago burbs to embrace integration, stemming white flight by insuring fearful homeowners against falling property values. Resident Christine Vernon, 55, recalls how the area "was lily-white when I was growing up. Today it's an international community." Houses range from $250,000 bungalows to million-dollar Queen Annes and a handful of Frank Lloyd Wright classics.

Naperville, 45 minutes further west, boasts a high school that topped rivals in 64 countries in the International Mathematics and Science Test. Jeff and Tamara Burke, both teachers in the system, bought their two-bedroom town house for $150,000 direct from the seller last year. "We used to go out here after dances in high school," says Tamara, 25. "I don't think it's changed much."  Top of page

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