The South Side of Chicago has always had a raw deal, cursed with the presence of bad-neighbor heavy industries like the sprawling Chicago Stockyards , the slaughterhouses and meatpackers that Upton Sinclair exposed in his 1906 novel The Jungle , and whose stink covered most of the South Side until the 1950s. The overriding impression is one of misery and downtrodden poverty, with block after block of deprived and dangerous neighborhoods. That said, there are exceptions: not just the Prairie Avenue and Hyde Park districts, but also the buzzing Chinatown around Wentworth Avenue and 22nd Street; the artsy, predominantly Mexican Pilsen district, a few blocks north and west; and the largely Irish, blue-collar Bridgeport , around Halsted and 37th - Mayor Daley's old fiefdom, the home of Comiskey Park and baseball's White Sox. To reach the South Side, double-decker Illinois Central commuter trains run beside the lake to Prairie Avenue (a block from the 18th St station) and Hyde Park (near the 59th St station). CTA bus #1 follows Michigan Avenue to the same places. Bus #8 runs every fifteen minutes, 24 hours a day, south through Pilsen to Bridgeport.

Two blocks east of Michigan Avenue, a mile from the Loop and only a quarter of a mile from the lake, Prairie Avenue started life as an exclusive suburb. Though just ten minutes' walk south from Grant Park and the Field Museum, it's best reached by cab, bus or train; the route is confusing and the streets are just not safe. As the one part of Chicago to remain unscathed in the Great Fire of 1871, this area had a brief moment of glory as the city's finest address. However, by 1900 the railroads had cut it off from Lake Michigan, and the expansion of the stockyards had encouraged the wealthy to flee back to their traditional North Side haunts.

One of the few structures to have survived the intervening years is the Romanesque 1886 Glessner House , Chicago's only surviving H.H. Richardson-designed house, standing sentry on the southwest corner of Prairie Avenue and 18th Street. Behind the forbidding stone facade, the house opens onto a garden court, its interior filled with Arts and Crafts furniture and swathed in William Morris fabrics and wall coverings. The place is maintained by the Chicago Architecture Foundation, which gives guided tours (Wed-Sun noon-3pm; $11 joint admission with Clarke House). A block away stands Chicago's oldest building, the Clarke House at 1855 S Indiana Ave (details as for Glessner House), a plain white 1836 Greek Revival pioneer home that spent many years as a community center before being gussied up as a minor museum of interior decor. Much more interesting, and proof of the wealth once concentrated here, is the lavish Gothic Presbyterian Church , a block away at 1936 S Michigan Ave, with its Burne-Jones and Tiffany stained-glass windows.

An island of middle-class prosperity surrounded by urban poverty, Hyde Park is the most attractive and sophisticated South Side Chicago neighborhood. It's also one of the more racially integrated areas of the city, and among its more erudite: the University of Chicago , endowed by Rockefeller in 1892 and now among the top institutions in the US, has encouraged a college-town atmosphere, with bookshops and numerous cafés around its compact campus, especially along East 57th Street. On the campus itself, two buildings are well worth searching out: the massive Gothic pile of the Rockefeller Memorial Chapel , at 59th Street and Woodlawn Avenue, and the Prairie-style Robie House , designed by Frank Lloyd Wright, two blocks north at 5757 S Woodlawn Ave. Campus tours start from the Ida Noyes Hall, 1212 E 59th St (Mon-Sat 10am).

Woodlawn Avenue runs north from the University of Chicago campus, passing one of the South Side's most popular taverns, Jimmy's Woodlawn Tap at 1172 E 55th St, before turning a whole lot grander. Besides its enormous mansions, Woodlawn Avenue illustrates the social and racial mix for which Hyde Park is renowned. Within two blocks of each other are the Midwest's largest Jewish temple, the ornate Isaiah Israel at 1100 E Hyde Park Blvd, and the home of Minister Louis Farrakhan , leader of the Nation of Islam, which was started here on the South Side in the 1940s by the late Elijah Muhammad. In between, at 4944 S Woodlawn Ave, stands the huge brick manor where boxer Muhammad Ali lived for many years.

Just west of the university, on the eastern edge of lush Washington Park, the Du Sable Museum of African American History , 740 E 56th Place, takes a look at the experience of Americans of African descent, from slavery to the present day (Mon-Sat 10am-5pm, Sun noon-5pm; $3; ). Named for Jean Du Sable, the Haitian-born Francophone who was Chicago's first permanent settler, it focuses on the works of WPA-sponsored artists of the 1930s and on the civil rights movement of the 1960s.

Washington Park wraps around the south side of the University of Chicago campus, to join the long green strip of the Midway - one of the few reminders that in the late nineteenth century Chicago was the site of the World's Columbian Exposition . Attracting some thirty million spectators in the summer of 1893 (45 percent of the US population at the time), the Midway was then filled with full-sized model villages from around the globe, including an Irish market town and a mock-up of Cairo complete with belly dancers. These days it's used mainly by joggers and students tossing Frisbees. A short stroll east, in Jackson Park, the cavernous Museum of Science and Industry , 57th Street at Lake Shore Drive (summer Mon-Fri 9.30am-5.30pm; rest of year Mon-Fri 9.30am-4pm, Sat & Sun 9.30am-5.30pm; $9; free on Thurs; ), was Chicago's single most popular tourist destination (and ranked second in the US) until it started charging admission in 1991. Besides interactive computer displays, the best of which explores the inner workings of the brain, exhibits include a captured German U-boat, a trip down a replica coal mine, and a simulated space-shuttle journey. It's fun for kids, but adults may not feel like staying very long. The complex also hosts a giant OMNIMAX movie dome; admission is $6 extra.

Promontory Point juts into Lake Michigan east of the museum, giving great views of the Chicago skyline, including a close-up look at Mies van der Rohe's first high-rise, the Promontory Apartments at 5530 S Lake Shore Drive.

South Side

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