You may not get any more quintessentially Chicago than Bridgeport, which was home to five mayors including the Daley clan. Working class with succeeding generations staying in the neighborhood, Bridgeport is seeing a little of the hipster spillage leaking over from Pilsen, but not enough to change its DNA. Irish, Lithuanian and Polish culture are still represented and since all of Chinatown is located in Bridgeport, you can safely say it’s a truly diverse community. Polo Cafe is just the best for breakfast; get a decent dog or the specialty of the south side, the Mother-In-Law sandwich, at Johnny O’s; or visit Bridgeport Coffee Company which has emerged as a contender in the competition among city roasters. Bridgeport Art Center attracts many artists to the community. Just remember that this is the south side, so whatever you do, don’t don a Cubs hat in these parts.
Home to the University Of Chicago and some guy named Obama, Hyde Park boasts plenty of brainy culture: Court Theatre, Museum of Science and Industry, Oriental Institute, Frank Lloyd Wright’s Robie House and the perfectly dubbed Smart Museum. The birthplace of atomic fission, Hyde Park is lined with wonderful Victorian homes and stunning parks. When visiting, stop in the historic 57th Street Book Store. The 57th Street Art Fair, held each June, is Chicago’s oldest juried art fair. Stop at Piccolo Mondo, a favorite of University of Chicago profs and Nobel laureates, with lovely views of the Museum of Science and Industry and Jackson Park.
Near Northwest Side
The name of the community and the 200-plus-acre park that celebrated landscape architect Jens Jensen’s design, Humboldt Park was a touchstone for Poles and later Puerto Ricans. Ride your bike through the park, hike the walking paths around the lagoon, watch kids play at the numerous baseball diamonds or slam some at the tennis courts. New indie shops are popping up every month in the neighborhood (try Humboldt House or An Orange Moon), and when you get hungry, don’t miss authentic Puerto Rican dishes at La Palma or La Plena. Consider ordering the iconic Jibarritos sandwich with your choice of meat, lettuce, tomato and garlic in between plantains instead of bread.
Related: Historic Walking Tours Of Chicago
Once a German enclave and home to DANK-Haus German American Cultural Center and a fragment of the Berlin Wall, Lincoln Square still offers a few Teutonic delights at Lutz Café & Bakery and sausages and schnitzel at Chicago Brauhaus. The community hosts a number of popular events every year including May Fest, Ribfest, Folk and Roots Festival, German-American Fest, a fall apple celebration and Lincoln Square Christkindl Market. Lincoln Square is home to mayor Rahm Emanuel, the Old Town School of Folk Music, tons of taverns along Lincoln Avenue and Half Acre Brewery.
With residents born in Mexico, Thailand, the Middle East, Pakistan, India, Korea, Somalia and so many more points on the planet, Albany Park is known as one of the most ethnically diverse communities in the country. Lawrence Avenue in Albany Park is sometimes called “Seoul Drive” because of a preponderance of Korean-owned businesses. Stop in at Lawrence Fish Market for the freshest sushi offered in a place you might not otherwise consider for raw fish (take out and cash only). You can find everything from falafel to Filipino garlic rice at low prices in Albany Park eateries.
Related: Walking Tour Of Chicago’s West Town