Tag Archive for Best of the South Side


Boarded-up storefronts not withstanding, 63rd Street is a pretty happening place. A terminus of the Green Line, “L” cars rumble above Cottage Grove. Underneath, Daley’s serves up steaming omelets, as it has since the restaurant opened in the 1930s. But the food, shoes, and booze end after only three blocks, and the activity comes to a dead stop.

The South Loop

From far away, the towering condo buildings of the South Loop appear crystalline and new, the products of more than 30 years of development. Yet the streets tell a much different story, worn by the highs and lows of the neighborhood’s past. Once the place to live in Chicago, Prairie Avenue hosted some of the city’s most recognizable families, including the Pullmans and Fields.


Bridgeport is one of Chicago’s “up-and-coming” neighborhoods. New foodie havens, a booming arts scene, and hopping nightlife beckon twenty-somethings and art types from across the city. While it is certifiably hip, Bridgeport feels strangely isolated from its surrounding communities in terms of geography and character, which gives it a quirky, organic hometown vibe.


Before the airport was built, the railroad drew working families to the area west of the Grand Trunk tracks. To this day, West Lawn remains a small but vibrant cultural center for Lithuanians in Chicago and beyond–home to the Balzekas Museum of Lithuanian Culture and one of the only Lithuanian-language printing presses in the country.


New boutiques, restaurants, and hangouts have gradually begun to emerge out of the buildings that once held the thriving Black Metropolis. While the golden days of poets and jazz are gone, today a bold community is committed to keeping its history, independence, and ingenuity alive.

Greater Grand Crossing

In 1853, two trains riding along rival lines collided at what is now the intersection of 75th and South Chicago Avenue. To prevent future crashes, the government mandated all trains to stop at the crossing, bringing in hundreds of visitors daily. Since that time, nearly half the area’s population has slowly bled away. Nonetheless, a critical mass has gathered along the area’s commercial thoroughfares.

Pilsen & Little Village

Pilsen and Little Village are cousins–not only because families often extend across the neighborhood boundaries, nor simply because they are both port-of-entry regions for recent Mexican immigrants. These two are a pair, now more than ever, because of a growing exchange between the two.


Originally dubbed “Beverly Hills” in reference to a massive prehistoric ridge that spans it, the neighborhood has always been home to more upwardly mobile middle class families than California-style celebrities. Today, while the outskirts of the neighborhood are home to commercial development, a continuous stream of traffic, and sun-baked sidewalks, the heart of Beverly continues to provide a respite from Chicago’s harsh urban scenery.