In the lush, winding Women and Children’s Park in the Prairie Avenue Historic District, kids play hide-and-seek near a bubbling fountain while day camp counselors mediate tiffs between toddlers. A mother of two pushes a stroller, picking a few apples from one of the garden’s trees and stowing them in her backpack. 

“I’ve already baked two pies,” she admits.

The scene is peaceful, bucolic—it’s hard to believe that it unfolds just blocks from the pulsing commercial center of Chicago. The South Loop, or “Sloop,” as it is commonly called, stretches from the Stevenson Expressway to Congress Parkway and from the lake to the Chicago River. The area has seen waves of affluence and decades of desolation, high culture and heavy crime over the last century. In the past two years, after suffering through the 2008 housing crash, a tight-knit community has begun to spread its roots in the Sloop, reflecting a desire among Chicagoans to live, once again, in a commercial center.

That’s the mindset of Emily Mooney and her husband, Todd, recent transplants from Lombard, Illinois, who moved into a condo apartment on Michigan and Roosevelt in September. Mooney, a lover of cities who got her undergraduate degree in urban studies, wanted to be in a place where she could take full advantage of Chicago’s cultural offerings.

“I wasn’t trying to live anywhere fancy,” she said. “Just somewhere urban.” Ready to leave the suburbs, Mooney shied away from other North Side neighborhoods—many annexed suburbs themselves—which felt isolating.

This isn’t the South Loop’s first stint in the residential spotlight. In the mid- to late nineteenth century, Prairie Avenue was prime real estate. The 1800-2100 blocks of this street are where Chicago’s wealthiest industrial engineers and entrepreneurs—George Pullman, Marshall Field, and Philip Armour, to name a few—made their homes, leading to the neighborhood’s nickname: “Millionaire’s Row.”  That was the case until the early twentieth century, when noise and pollution from booming printing, publishing, and auto industries began to encroach, and proximity to the Loop began to be seen as a disadvantage rather than a boon. Moneyed Chicagoans moved north and south, taking up residence in neighborhoods that provided them access to—but also considerable distance from—the city center.

The Sloop’s revival as a residential area can be seen in community projects such as Sloopin’, a popular blog devoted to “all that is and could be life in the South Loop.” South Loop residents post on a daily basis about everything from store openings to food drives to photo contests. The blog’s founder and editor, Ryan (who declined to give his last name), started Sloopin’ after moving to the area from the North Side in 2008 and finding a dearth of consistently updated information on the neighborhood. Like Mooney, he extols the benefits of the South Loop’s central location. For him, proximity to the lake, CTA, Grant Park, and Museum Campus—where he often picnics on the grass with his family—are hard to beat.

“If you’re living in Chicago, and you like Chicago, you want to live in Chicago, not Chicago-light,” he said. Ironically, he says, the area is quieter than some of the busier North Side neighborhoods, like Wicker Park or Lincoln Park, where blocks are nightly flooded with bar and restaurant-goers. “It’s not really a destination yet,” said Ryan, “and a lot of people like that.”

The diversity of the South Loop’s current population is also a draw for many. Mooney, who says parts of the North Side felt like a “lily-white enclave,” appreciates the racial and cultural variety in the neighborhood. South Loop citizenry, according to Ryan, including its share of young professionals, is balanced between college students, retirees and—increasingly—young families like his own. “You see a lot of babies and dogs around here,” he said.

This is not to say the South Loop is homogenous, consisting of several small but distinct neighborhoods, each—like Prairie Avenue—reflecting a different episode in South Loop history.

Printers Row, which runs along Dearborn between Congress and Polk and was once the heart of Chicago’s literary industry, exemplifies the South Loop’s efforts to preserve its past while catering to new residents. The red brick Donohue Publishing House has been converted into loft housing. The Old Dearborn Station, the oldest train station still standing in Chicago, has been turned into retail and office space. The rustic exterior now houses doctors’ offices, legal practices, and a ballet studio.

Even Sandmeyer’s Bookstore, a neighborhood staple since 1982, seems to be straddling two worlds. Exposed brick and pipes on the ceiling hark back to an earlier time, but the books, mindfully arranged on metal racks, angled somewhat sparsely throughout the single room, are all new.

At times, the old Printers Row feels somewhat abandoned, with historical remains blending in among new growth. That isn’t necessarily a turnoff, though. “I kind of like the ghost-town vibe,” said Mooney.

Other parts of the South Loop more actively celebrate the neighborhood’s past. The exclusivity that once defined the Prairie Avenue Historic District seems to have disappeared along with Pullman and Field. Posters detailing the history of the homes and restoration line the streets, and tours of the inside of the Clark and Glessner Houses are available to the public.

Meanwhile, the Clark House backyard has been repurposed as the Women and Children’s Park, from which, on a recent afternoon, the shouts of kids from the local soccer league could be heard hawking their wares from a lemonade stand nearby. The South Loop may well be a place where history and community can coexist among big business and new development. It certainly looks that way from the Mooneys’ living room window, where, from twenty-five floors up, Emily and Todd can see both Grant Park and the train tracks that hauled freight and passengers into the city over 100 years ago.

Among the cluster of facades on South Michigan Avenue perches a lofty gathering ground for piano devotees. Three floors high, PianoForte offers a carefully chosen assortment of acoustic and electric pianos. They are displayed with artful intent throughout the first floor, like religious artifacts of ancient importance. The store is curated by friendly aficionados, eager to get to know you and guide you toward the perfect match.  Options range from top of the line, pro-endorsed models with jaw-dropping design, sound, and price tags, to a line of more accessible pre-owned instruments. The second floor functions as a recital hall, hosting a piano-centric menu of live performance. The PianoForte Salon series offers a chance to both hear and meet world-class pianists, while their new Storytellers series offers a genre-spanning array of musicians blending live music with personal narrative. They also host kid-friendly events, in which piano demonstrations are supplemented with discussions about performance and music (also milk and cookies). If you are a pianist, or just an enthusiast, stop in. “Ode to Joy” will come rushing to your ears. PianoForte Studios, 1335 S. Michigan Ave. Showroom hours: Tuesday-Saturday, 11am – 6pm. (312)291-0291. pianofortefoundation.org (Zach Upton-Davis)

Reggies Chicago
Reggies has one of the most idiosyncratic music programs in Chicago. On the one hand, they love heavy metal: no other South Side venue is as likely to host bands with names like Pentagram (October 23), Bloodletter (October 28), or Metalucifer (November 28). On the other hand, they have a sixth sense for finding up-and-coming hip-hop acts and putting them on stage. Part of this has to do with their frequent partnerships with the local hip-hop blog Fake Shore Drive, which regularly showcases Chicago artists at the venue. Reggies’ last FSD showcase helped introduce many to Mick Jenkins, the South Side rapper whose recent mixtape, The Water[s], might be this year’s best Chicago hip-hop album. It’s also played host to some hectic shows from local stars like Alex Wiley, Chance the Rapper, and Chance’s younger brother Taylor Bennett. Yet Reggies’ programming isn’t strictly local. They also draw in some widely respected acts like the Detroit producer Black Milk, who will be coming to the venue on October 24. Overall, Reggies may be the best place to go for hip-hop if you’re trying to escape from the Shrine’s fixation with the nineties Golden Era and are looking for something more contemporary. If you’re in a nostalgic mood, though, there is also something for you: Reggies is still sporadically hosting its “Elton John Album Nights,” in which Simply Elton John, aka singer and celebrity impersonator Brian Harris, revives various deep cuts from the Rocket Man’s catalogue. Reggies, 2109 S. State St. Sunday-Friday, 11am-2am; Saturday, 11am-3am. (312)949-0120. reggieslive.com (Zach Goldhammer)

When most people think of Chicago cuisine, hot dogs and deep dish likely come to mind before Cuban flavors. Unless, that is, they’ve eaten at Cafecito. Located at 7 North Wells Street, just off South Wabash, the homey establishment serves up a menu chock-full of the best sandwiches in the South Loop. Creations like the guava-q (roasted pork or chicken, caramelized onions, and guava BBQ sauce) and the ropa vieja (skirt steak, sweet plantains, black beans and tomato Creole sauce) mix Latin ingredients in a myriad of combinations, none of which will put you out over $6.50. And it doesn’t end there: Cafecito’s menu is complete with sides, salads, and perilously creamy batidos. The caldo gallego soup, featuring ham, collard greens, white beans, potatoes, and onions in a spicy broth, could thaw through any Chicago winter chill. You can get your caffeine fix with one of their Cuban-style coffee drinks, including their signature “cafecito,” a shot of espresso with what they claim is a teaspoon of sugar—though it tastes more like three. The lunch crowd is regular and hungry—the line is out the door by 12:30—so get there early or be prepared to wait. Then grab a seat at a table, armchair, or plush green couch, or take your butcher paper-wrapped treasure to go. Cafecito, 7 N. Wells St. Monday-Friday, 7am-9pm. $2.99-9.85. (312)922-2233. cafecitochicago.com (Hannah O’Grady)

Printers Row Literary Festival
For one weekend every June, thousands of the city’s readers flock to Dearborn Street for their yearly allotment of all things books. From a workshop on the pamphlet stitch to readings by Chicago’s favorite storytellers to handmade, leather-bound journals to first-edition Penguin paperbacks, the Printers Row Literary Festival has it all. The weekend would feel like a step back in time—with “M.A. Donahue” still studded across the once-prestigious printing press building and the Dearborn Street Station majestic behind tents of comics and zines—except that Chicago was never quite as literary as it is during Printers Row. The festival transforms the neighborhood from a quiet community to a hub of activity, and Chicago’s authors, printmakers, editors, and readers come to greet it with open arms. Tents holding University of Chicago Press and Northwestern Press titles, Powell’s Books, and independent presses mix academic with trade. The weekend leaves festivalgoers with an armful of books and the elation that only comes from the mass exchange of stories. Printers Row Lit Fest, Dearborn and Polk St. Annual. Next year’s festival will be June 6-7, 10am-6pm. Free. Tickets required for indoor programs (Claire Gillespie)

18th Street Bridge
During construction for the 1933 Century of Progress World’s Fair, a roundabout footbridge was built over the South Loop’s rail yards and scrapyards to grant access to the lakeshore’s attractions. It remains to be seen how many more centuries of progress will be necessary to devise a less bogus route to the shore anywhere between Roosevelt and 31st. This is easily the sparsest set of pedestrian access points to the lakefront path anywhere along its eighteen-mile length. In such a densely populated, attraction-rich area, that fact makes about as much sense as handing out a heap of free land to George Lucas so he can build a museum full of Stormtrooper helmets. West access to the crossing is from Calumet and 18th (a proposed location of the Battle of Fort Dearborn, and just a block away from the Women’s Park and Gardens). First, one is led beneath a service road; next, in order to surmount the Illinois Central trackage, the path forms two ascending hairpin curves rising ever-so-slowly to a considerable height. A rickety staircase leads down to a whistle-stop Metra platform, while the main path continues east to ground level. From there, you can proceed under Lake Shore Drive to the southern tip of Museum Campus. Alternatively, you can head south through a desolate plaza and pick up a sneaky, maybe-legal road into the underbelly of McCormick Place. (Not recommended during a NATO summit.) In the end, you will have spent ten minutes moving a couple hundred feet, but at least you had some time to reflect on the intricate pressures that shape the ways we get around the city: the lay of the land, infrastructure old and new, expanding private enterprise, and Chicago’s laudable but fraught commitment to a public, accessible lakefront. 18th Street Bridge, from 1800 S. Calumet Ave. to 1600 S. Lake Shore Dr. Access at all times. No motor vehicles (Andrew Lovdahl)

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