Showing up at a 4 a.m. bar when it opens is like standing in line for the midnight screening of a movie no one wants to see. Either way, you’ll end up in a dark and nearly empty room for the span of several hours, so early for the party that you end up feeling late for something crucial. I had arrived at The Owl (2521 N. Milwaukee Ave.) with a plan to document one full night of the bar’s comings and goings, one eight-hour slice of life at one of Logan Square’s most notorious dive bars. Surrounded by empty leather stools, my stream of thoughts trickling into the waterfall behind the bar, I started to wonder if that life was really very interesting, after all.
According to the City of Chicago’s Department of Business Affairs & Consumer Protection (BACP), Chicago is home to approximately 200 late-hour liquor establishments. Such establishments are allowed to sell liquor until 4 a.m. on weekdays, a stipulation that has given rise to the colloquial term “4 a.m. bar.” This term has taken on a nefarious life of its own, becoming synonymous with bedlam, debauchery, and general excess. The BACP seems to agree with this popular assessment, which is why it requires every licensed 4 a.m. bar to operate with something called an “exterior safety plan.” Among more basic concerns, the plan requires security personnel and the installation of surveillance cameras at all entrances and exits. It says something about the fortitude of your average late-night carouser that these are considered necessary measures.
As the bartender poured my second of many Old Styles, I asked him—a tattooed 20-something in a sleeveless Black Sabbath shirt—to answer a few questions. These might have sounded harmless enough, were they not coming from someone sitting in a late-night bar at dinnertime, eyeing every inch of the place as if planning a grand heist. Much to his credit, he introduced himself as Billy and played along without a hint of suspicion. Asked if The Owl was outfitted with standard security cameras, he nodded in affirmation. “You actually don’t have to have them,” he explained, contradicting my friends at the BACP, “but you’re an idiot if you don’t.” Looking around, I counted at least 30 statuettes and framed paintings of owls. Their wide, round eyes all seemed to fixate on the bar, and I imagined dozens of tiny cameras capturing my every sip.
If that was truly the case, there wasn’t much to record at first. A couple drifted in for post-dinner cocktails around 9 p.m., but things remained otherwise quiet on the customer front. Sensing my unrest, Billy offered a reassuring smirk. “People usually start to trickle in around 10:30,” he said. “On average, things really get cranking around 1:30.” To pass the time until then, he entertained some questions about the bar’s history. I was most interested in how the place had acquired its late-night license, and the answer was simple enough: it hadn’t. At least, not in the traditional way. Not quite two years ago, The Owl’s Milwaukee Avenue storefront was home to a rowdy Mexican dance club called La Estrella. When that place closed its doors, the late-night license transferred to the building’s new tenant. Just like that, Logan Square’s newest 4 a.m. bar was born.
I was starting to regard the clock on my wrist as a sworn enemy when the first large group walked through the door. Dressed in jean cutoffs and plaid button-ups, they seemed to fit right in with The Owl’s backwoods-lodge-meets-Belle-Époque-Paris vibe. One girl seated beside me at the bar—somewhat of a regular, from what I gathered—described The Owl in her own way: “You know, I could see this place existing in Twin Peaks.” She was quick to point out some of the David Lynchian qualities I had missed. “Have you noticed that there are no mirrors in the front room, but that entire back room”—she pointed to the emptiest, most dimly lit section of the bar—“is lined wall-to-wall with them? That says a lot about the kind of people who hang out back there.”
It’s easy to imagine those vaguely creepy mirrors as a holdover from the La Estrella days, but my friend had a point. Another hour passed—we’ve reached midnight, for those keeping score—and a crowd of well-dressed club-goers descended on the bar like thirsty locusts. These were the glamorous fedora-and-updo types who go out on a Wednesday to see and be seen, and no sooner had they arrived than the back room’s unseen disco lights turned on, a DJ set up his turntables, and the place turned into something resembling a dance club. Two new security guards showed up to keep an eye on the crowd, which swelled with each passing minute. We had arrived at the late-night portion of the late-night bar.
Hipsters, yuppies, townies, bewildered suburbanites—come 2 a.m., each group was well represented in at least one darkened corner of The Owl. It was a refreshingly diverse crowd made possible by sheer circumstance; when every other bar within a mile closes, the options for drinking within your scene become severely limited. This, I think, is where the true appeal of the 4 a.m. bar lies. It’s the Wild West meets the United Nations, a place where anything goes (within the limits of the guards’ patience) and where the next stranger you meet might as well be from another country.
It’s also the province of some strange recurring characters who seem to show up on a nightly basis. One is the ubiquitous Tamale Guy, whose whereabouts are tracked on Twitter, and whose cooler of home-cooked treats rarely lasts long in a crowd of hungry drinkers. Another is a man who looks altogether confused, holding an old-timey camera and gesturing to strangers to see if they’d like their photos taken. The answer is usually, “No, thanks,” but that doesn’t seem to deter him.
Such eccentricities, mixed with a dozen or so Old Styles, had won me over by the time the guard screamed “Last call!” They’re not for everyone—and they’re certainly not for every night—but 4 a.m. bars occupy a fascinating niche in Chicago’s nightlife that’s worth exploring (albeit, in a less masochistic way than I’d chosen). Few other places promise the same erratic cross-section of humanity, the same potentiality to just get weird. Provided, that is, you can stay awake.
Illustration: © Will Landon, Groupon