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. At the turn of the 20th century, however, factories moved in, and the area’s wealth gravitated north to the increasingly affluent area along the Gold Coast. All but eleven of the original houses on Prairie Avenue were demolished to make way for printing factories, manufacturing plants, motor show rooms, and low-income boarding houses.
With the decline of one community came the rise of another. The studios of Record Row on South Michigan Avenue recorded some of Chicago’s seminal artists, from Muddy Waters to Memphis Slim to Bo Diddley. Sprinkled across the surrounding neighborhood were vibrant blues, jazz, and soul clubs, a scene ignited by the Great Migration that was rapidly transforming the entire South Side.
Since the 1960s, developers have moved in to build the South Loop up and up. The boxy behemoth McCormick Place has drawn massive numbers of business travelers to the neighborhood. New townhouses, vaguely reminiscent of the Prairie Avenue extravagance of old, line many side streets. Amid the recently constructed high-rises, hints of the neighborhood’s past sit tucked in worn storefronts and down back alleys. Don’t be blinded by the sheen of the new steel and glass towers–despite the many twists and turns of Chicago’s past, the South Loop has been here since the start.
Best Time Machine
The Glessner House Museum
The Glessner House belongs to a different Chicago. Billowing smokestacks, corrupt politicians, rough-and-tumble streets, this Chicago followed the tides of industrial progress. The home’s stone fortress faÃ§ade is unmistakable. Windows like arrow slits and a wall of giant granite impose on the street a sense of awe and fear. Designed by American legend H. H. Richardson (famous for the Trinity Church in Boston), the home was built in 1885 for businessman John Glessner and his family. Glessner was an early champion of the Arts and Crafts Movement, reflected at every turn inside the house: intricate woodworking by Isaac Scott, ornate silver pieces, imported English textiles, and even a lavishly inlaid Steinway. Amid these proto-modernist details, it is easy to see the house’s influence on such architects as Louis Sullivan and Frank Lloyd Wright. The garrison-like exterior of the house protected the Glessner family from the cruel streets of the growing industrial district, while the inside showed off the opulence that was its fruit. The contrast between this warm interior and the imposing walls outside strike a chord about that old Chicago–the tensions between industry and nature, and the stark divide between rich and poor. Walking through the house you get a sense of how far the city has come. Or, depending on your view, how little. 1800 S. Prairie Ave. Wednesday-Sunday, 11:30am-4pm. (312)326-1480. glessnerhouse.orgÂ (Isaac Dalke)
Little Branch CafÃ©
With old tree stumps-as-barstools, Little Branch CafÃ© offers its patrons a surprisingly organic experience within the faceless glass of a new high-rise. The dark wood floor and stylish paper light fixtures create a cozy atmosphere to enjoy in-house and locally made pastries and coffee. Still, it strives to be much more than just a high-quality coffee shop. The cafÃ© offers a full-service bar and a gelato counter. Wednesday through Friday, Little Branch even serves a modest dinner menu, with entrees such as “Chicken & Waffles” and a croque-monsieur crepe. It’ll come as no surprise that their delicious hot paninis are aimed at the lunchtime office crowd. Slowly expanding operations since it opened in 2007, Little Branch is quickly turning into the South Loop’s best spot for light fare. And, as the name suggests, it’s a great place to alight for a rest after a tiring day. 1251 S. Prairie Ave. Monday-Tuesday, 7am-4pm; Wednesday-Friday, 7am-10pm; Saturday, 8am-10pm; Sunday, 8am-4pm. (312)360-0101. littlebranchcafe.comÂ (Isaac Dalke)
Reggies Rock Club
For anyone looking for a taste of Chicago’s gritty rock scene, Reggies is the city’s go-to venue south of the Loop. Whether punk, hard rock, metal, grind core, or eclectic fusions, Reggies reels you in week after week as a three-in-one record store, music joint, and rock club. The 21+ music joint offers a full bar and restaurant with a mini stage that features smashing late-night sets. The more cavernous all-ages and 17+ rock club next door has hosted big names such as L.A. Guns, Brit punk legends the Adicts, and underground thrash metal masters DRI. If you ever find yourself wandering around the South Loop, keep your eyes open for a mash of leather, mo-hawks, piercings, and tattoos taking a smoke break. Follow the crowd in through the pitch-black doorway, pass by the merch booth and anchor yourself next to the giant speakers with a good pair of earplugs. Don’t worry, even the regulars take such a precaution. But if you need to feel a bit tough, the moshing won’t be too long coming. 2105 S. State St. See website for show times and cover charges. (312) 949-0120. reggieslive.com (Marina Grozdanova)
Willie Dixon’s Blues Heaven
The Rolling Stones’ track “2120 South Michigan Avenue” grooves atop a punchy guitar and soulful harmonica. A steady beat completes the quick, fun number,Â framing the interplaying treble. However, the actual 2120 South Michigan Avenue, now Willie Dixon’s Blues Heaven Foundation, would be better immortalized by a three-part epic. Once the home of Chess Records, the old studio recorded blues hits by the likes Dixon, Howlin’ Wolf, and Muddy Waters. However, by the late 60s Chess was mired in a royalties controversy and eventually succumbed to financial ruin. Boarded up, the building was purchased in 1992 by Dixon’s widow to house the foundation her husband created before passing. The foundation now serves as an office, museum, and concert venue. Inside, memorabilia from the Chess Records era covers the walls. In the back rooms, the foundation organize programs to assist aging blues musicians while supporting up-and-comers. Outside, in an enclosed pavilion called the Blues Garden, they host blues concerts in warmer months. 2120 S. Michigan Ave. Tours available Monday-Friday, 11am-4pm; Saturday, 12pm-2pm. $10. (312)808-1286. bluesheaven.com (Tyler Leeds)
Best Place to Spot a Snowy Owl
Northerly Island (actually a peninsula) hosted Chicago’s second World’s Fair in 1933-1934 before it was converted into an airport. Eighty years later, that airport, called Meigs Field, entered into Chicago political lore when former mayor Richard M. Daley controversially bulldozed the runway under the cover of night, stranding sixteen aircraft on the tarmac. The move cleared the way for completion of a small holdover from the 1909 Burnham Plan. After nearly a century, the island offers a glimpse of Burnham’s grandiose vision of converting the city’s islands into parkland. Wild prairie hosts native flowers and the island is a stopover for migratory birds (and the best place in the state to spot a snowy owl). A stroll along the island’s paths reveals one of finest views of Chicago: the downtown skyline rising up at a distance from behind tall, windblown grass. If you don’t make it there by the time snow blankets the island, grab a pair of cross-country skis at the island’s field house–the views will still be astounding, if a bit bleak. 1400 S. Lynn White Dr. Field house open Monday-Sunday, 9am-5pm in the late spring, summer, and autumn; Saturday-Sunday, 10am-5pm in the winter and early spring. (312)745-2910 (Gregor-Fausto Sigmund)