South Loop

There is a spot on Roosevelt Road, near the northwestern edge of the South Loop, where you can see the buildings of the Loop in the distance and a tangle of train tracks in the foreground. Turning to the south reveals a dispersed array of towering residential complexes. This panorama encapsulates both the history and current identity of the South Loop, a relatively small neighborhood with a lot of potential but few defining characteristics. The lingering train tracks recall the days of the late nineteenth and early twentieth centuries, when freight and passenger trains dominated the area’s industrial landscape. The remote Loop skyscrapers symbolize a fundamental disconnect: the South Loop is not quite part of the city center, and despite its various classifications, not quite part of the traditional South Side. When asked about what area his business caters to, the owner of the Printers Row Wine Shop said “South City”—a term that only adds to the region’s vague character.

The residential buildings represent the South Loop’s current makeup to some extent, but point even more to the future. It isn’t hard to understand why—apartment buildings can be found on almost every street, and proximity to the businesses of the Loop make the South Loop a perennially attractive place to live. The story that is more difficult to recognize is that the 2008 housing market crash hit the South Loop hard; virtually all development screeched to a halt. Fortunately, things are finally looking up again. Over the past year or so, the South Loop has experienced the city’s biggest gains in property values. Plans to build the first massive condo complex since the housing bubble are in the works, and the construction of a new Cermak Green Line station is underway, signaling a desire to attract visitors to McCormick Place and transform the area between the Roosevelt and 35th Street stations.

As people move into an area, restaurants, entertainment venues, and other amenities that give neighborhoods character inevitably follow. In his 2008 book “Who’s Your City,” Richard Florida argues that place still matters and globalization is exaggerated. In other words, people still need to move into exciting, vibrant places to realize their potential. If the South Loop is going to continue to attract new residents into its many apartments and condos, concrete developments will have to keep popping up. That should make for an exciting future, and hopefully the beginnings of a truly great neighborhood with its own distinct character.

BEST AFFORDABLE FANCY DATE RESTAURANT: City Tavern
Although the South Loop is not exactly overflowing with upscale restaurants, City Tavern is one of the area’s most underappreciated places to eat. Aside from the food, one of the best sensations that patrons experience is the very first one: walking inside the rustic, eighteent-century-style dining room and being greeted by bright chandeliers, a stunning mirrored bar, and a beautiful, meticulously crafted earthy color scheme that pervades every nook and cranny of the lower floor. Once you sit down, the menu boasts an interesting array of appetizers and side dishes, or “bites,” that can easily be used to construct a good meal. The cocktails are creative and the wine and beer list is extensive as well. However, City Tavern’s biggest advantage over other chic eateries in the South Loop, such as the often-cited Acadia, is that it can fill you up for less than twenty-five dollars. No miniature-sized portions—just interesting food at a good price. City Tavern, 1416 S. Michigan Ave. Monday-Thursday, 4pm-midnight; Friday, 4pm-1am; Saturday, 9:30am-1am; Sunday, 9:30am-midnight. (312)663-1278. citytavernchicago.com (Gabe Friedman)

BEST WINE DISPENSER SYSTEM: Square One
Just seconds from City Tavern is Square One, the South Loop’s best bar for cocktails. It is tempting to call it “the bar of the future” as well, because of its innovative layout and mechanical wine dispenser system. The wine machine, which holds various bottles of whites and reds behind glass panes, is embedded into a wall near one of the entrances . Patrons can request “wine cards,” which are the size of a credit card and contain fifty dollars of spending credit. The cards fit neatly into a slot on the red or white side, and wine is dispensed at the touch of a button. The experience is reminiscent of the outlandish technological amenities offered in science fiction, but maintains an approachable simplicity. Even if bar culture seems to be headed in this direction, for now, Square One is still a one-of-a-kind experience, especially in the sports-bar dominated South Loop. Square One, 1400 S. Michigan Ave. Monday, 4pm-midnight; Tuesday-Wednesday, 4pm-1am; Thursday-Friday, 4pm-2am; Saturday, 4pm-3am. (847)414-3699. squareonechicago.com (Gabe Friedman)

BEST EMBLEM OF PRINTER’S ROW: Sandmeyer’s Bookstore
It is only fitting that Printer’s Row is home to the South Loop’s best bookstore. The neighborhood was once the printing center of the Midwest, but the former printers’ buildings have steadily turned into residential complexes since the 1970s. However, one building is a ghostly reminder of the printing era that was. The words “M.A. Donohue & Co. Book Publishers” remain on the front of the iconic Donohue building on Dearborn Street, casting a literary shadow over the surrounding blocks. The tangible bearer of this bookish spirit is Sandmeyer’s Bookstore, a family-owned independent shop that has thrived across the street from the ghostly Donohue building for over thirty years. For a relatively small space, the store carries a large variety of books, from the latest intellectual fiction to children’s books and travel guides. The large sale section in the back corner offers great deals on choice books in perfect condition. Visit for these reasons—or maybe just for the old book smell that permeates the store in a neighborhood so steeped in literary history. Sandmeyer’s Bookstore, 714 S. Dearborn St. Monday-Wednesday, 11am-6:30pm; Thursday, 11am-8pm; Friday, 11am-6:30pm; Saturday, 11am-5pm; Sunday, 11am-4pm. (312)922-2104. sandmeyersbookstore.com (Gabe Friedman)

BEST SELECTION OF UNIQUE ALCOHOL: Printers Row Wine Shop
The beautiful walls of the Printers Row Wine Shop are lined with over a hundred bottles of wine, and the shelves in the middle of the store show off dozens of unique beers and spirits. This makes the fact that the shop’s two owners individually sample every single label that they sell all the more amazing. Founded just under ten years ago, the shop—which has a newer sister location in University Village—has cultivated a happy customer base thanks to these meticulous standards. The shop’s support of local producers and its free wine tastings on Fridays throughout the entire year (except for January: in one owner’s words, “no one does anything in Chicago in January ”) have helped spread the word and undoubtedly contributed to its success. Prices vary and can be expensive, but the wide selection of more reasonably priced vintages makes the shop a great destination for just about every type of wine lover. Printers Row Wine Shop, 719 S. Dearborn St. Monday-Wednesday, 11am-10pm; Thursday-Saturday, 11am-11pm; Sunday, noon-8pm. (312)663-9314. printersrowwine.com (Gabe Friedman)

BEST RAILROAD REBIRTH: Jazz Showcase
Rail travel and jazz clubs concurrently faded in Chicago during the latter half of the twentieth century, but relics of each have come to cohabitate in the redeveloped Printer’s Row neighborhood. The Jazz Showcase has been “Where Jazz Lives in Chicago” since 1947, but its move to Dearborn Station is recent. Inside, the club is dark (a good start), and a three-sided bar and an elevated stage anchor either side of the large room. The space between is filled with tables, chairs, and couches—room for 170 guests—that face the stage. (Note that the dive down to retrieve items swallowed by the couches may bring up some unexpected discoveries from the club’s history.) The bar offers a range of choices for all tastes, though the “specialty drinks” are sweet enough to make a sorority sister cringe and should be avoided. During weekends the club hosts better-known acts at a cost of $20-$45. The week, however, brings performers more humble as well as eager amateurs, who participate in open jam sessions for $10, $5 for students. Jazz Showcase, 806 S. Plymouth Ct. Monday-Saturday, 8pm-2am; Sunday, 4pm-2am. (312)360-0234. jazzshowcase.com (Tyler Kolle)

BEST ALTERNATIVE TO CHIPOTLE: Flaco’s Tacos
When your stomach says, “I could really go for some good Mexican food” and your habits tell you, “Chipotle would really fill me up,” but then your conscience adds, “hold up, remember how ill you felt last time we had an overly-salted burrito the size of a newborn child,” you should consider Flaco’s Tacos in the South Loop. It should be made clear that proportions are sufficient if not generous, but the wraps are stuffed with ingredients that haven’t been salted and left in a metal tray for an extended period. The selection is diverse—tacos, bowls, burritos, quesadillas, tortas with the option of a variety of meats (including fish), or vegetables for those who don’t have carnivorous inclinations. Service is fast and prices are reasonable ($2.50 for tacos, $7-$8 for a burrito). Beer, margaritas, and sangria can also be purchased if you’re looking to get a little boozy while you load up on reasonably authentic Mexican cuisine. Flaco’s Tacos. 725 S. Dearborn St. Additional North Side locations. Monday-Saturday, 10:30am-10pm; Sunday, noon-10pm. (312)922-8226. flacostacosonline.com (Tyler Kolle)

BEST ROCK MUSIC HANGOUT: Record Breakers
This is a store straight out of a Hollywood movie set, a rock music–lover’s dream. After twenty-five years in business, six in this location, Record Breakers’ dimly lit walls are well covered in collages and posters. Exotic rock memorabilia such as masks and blimps hang from the ceiling, and a floor conquered by crates of records, CDs, and VHS tapes makes linear travel a bit difficult. A polite and knowledgeable staff handles obscure record requests and guides inebriated patrons and hopeful band members (those seeking always-invisible booking agents) around the store. The majority of its selection is rock music, but it has a surprisingly large and well-curated classical section, culled primarily from the estate sales of the recently deceased. Browse the store late at night to hear live music vibrating through the floor from Reggies’s downstairs music club. And as you make your purchase, say hello to the red-gold sun canary squawking from its cage behind the counter, because why not? Record Breakers, 2105 S. State St. Monday-Sunday, 11am-midnight. (312)949-0125. reggieslive.com (Dove Barbanel)