A quintessential Chicago bar, Schaller’s Pump boasts a storied history that’s built on a foundation of baseball and politics. The tavern is a mainstay of Bridgeport in every sense of the word. It’s Chicago’s oldest continually running bar (since 1881) and over the years it has served as a shot-and-beer hangout for blue-collar workers, a pre-game dining spot for White Sox fans, and a hangout for the deal-making politicos that work across the street at the 11th Ward Democrats. Visitors walking up to the tavern should enter through the side door next to the parking lot; the large, arched-wooden door in the front of the bar remains shut at all times to ward off door-to-door encyclopedia salesmen. Once inside, visitors may not be blown away by the unassuming décor, but they’ll soon warm up to the cheap beer, singing old-timers, and menu of hearty eats such as butt steak and corned beef hash. However, the real draw is the chance to hear a good story. Owner Jake Schaller has lived upstairs for 35 years, and can talk anyone’s ear off with tales of illegal booze-running and Chicago big-shot sightings. For example, The South Side Brewing Co. operated next door during the Prohibition, under the guise of making non-alcoholic beer. Little did the authorities know that barrels of booze constantly rolled through underground tunnels connected to Shaller’s Pump. Future mayor (da mare, in Chicagoese) Richard Daley spent his 21st birthday here, and White Sox owner Bill Veeck used to stop in regularly for a cold brew. One time, Mr. Veeck took a $20 bill, covered one side with butter, put a silver dollar on the other side, and threw it (true it, in Chicagoese) at the ceiling. The bill supposedly stayed there for 20 years. It’s the type of longevity that makes this place so charming.
Housed in a tavern that dates back to the 1880s, Shinnick’s Pub is the product of three generations of family history. There are no beers on tap, but plenty of bottled domestics. Located in the shadow of U.S. Cellular Field, this Irish mainstay is liveliest in the hours following a White Sox win.
Ranked as some of the Best Barbecue in Chicago by CBS News, Honky Tonk Barbecue is the brainchild of pit-master, chef, and owner Willie Wagner. Within the Pilsen space, Wagner rubs and smokes his famous pulled pork for 17 hours, using the same recipe and technique that won him third place at the world Championship Barbecue Cooking contest in 2008. Barbecue-loving Midwestern crowds—and celebrity chef Guy Fieri—flock to Honky Tonk for not just the pulled pork, but also to sample bacon candy, beef brisket sandwiches, and bold slabs of dry-rub St. Louis ribs.
On an otherwise quiet corner of Chicago's Ukranian Village neighborhood, a crowd of 20-somethings spills out onto the sidewalk to smoke and mingle. Like its hipster devotees, The Empty Bottle seems to never sleep. The club keeps late hours and hosts bands or DJs nearly every night, from local showcases to celebrated dance parties such as the Windy City Soul Club. Even in the coldest months, the overfill spills out onto the sidewalk, where crowds huddle together for warmth beneath a black awning that reads “MUSIC/FRIENDLY/DANCING.” Inside, past the pool table and pinball machine, is a doublewide space and a small stage lit by multi-colored lights. Decorated with years of musical and barfly ephemera, the bar sits beneath a tilted chalkboard that displays the daily drink specials and beer offerings. The club prides itself on cheap drinks and cheap admission prices—all the better for checking out local acts you may never have heard before. Don’t try to take advantage of the staff’s friendliness, however, lest they decide to show you how the severed door of a CPD car came to hang above the exit.
Tucked away on a quiet block in East Ukranian Village, the unassuming façade of Happy Village make it easy to miss. But for those lucky to make their way through the swinging door, a sense of time traveling awaits. The vinyl floors and photos of JFK harken back to 1964, the year when Happy Village first opened. On any given night, bartenders crack open cans of reasonably priced PBR, Hamm’s, and Old Style. Opponents face off at the rear room’s ping pong table, while in the warmer months, groups gather in the backyard beer garden to marvel at the modern invention of stringed lights.
Bartenders at this no-nonsense cocktail spot make ‘em stiff and simple. The bar just may be the smallest in town—it measures 3.5 feet wide at its narrowest section and 15 feet wide at its roomiest. Still, loyal patrons happily squeeze in and order up a perfectly prepared Manhattan or margarita.