Getting Loopy: An Old-School Bar Crawl Through Downtown Chicago

October 13, 2017

By Dan Epstein, October 13, 2017

There are few pleasures simpler or more satisfying than an after-work beer. Whether you’re an avowed IPA snob or a loyal lover of the cheapest lagers – and whether you’ve spent the day seriously working your ass off, or merely pretending to look busy during another monotonous shift – quittin’-time suds somehow always taste better, especially when you’re enjoying them at a favorite watering hole just steps from your place of employment.

I first got hooked on workingmen’s bars in early 1980, when my then-stepfather took me to lunch at Chicago’s legendary Billy Goat Tavern. Located just a short stroll from the offices of both the Tribune and the Sun-Times, the subterranean saloon was packed that day with newspaper employees – some done with work for the day, some enjoying a little lunch and liquid refreshment before heading back to the office.

In between bites of greasy “cheezborgers” and gulps of cold Schlitz, they loudly talked shop, bitched about then-Mayor Jane Byrne, and argued about what the upcoming baseball season would bring for the Cubs and White Sox. I was only 13 at the time, but I loved the vibrant energy of the scene, and looked forward to the day when I would be old enough to grab a post-work beer with my co-workers in a similar sort of joint.

Located just across the Chicago River from the Billy Goat, the Loop – so named for the rectangular circuit of elevated railway tracks that run along Wabash Avenue and Van Buren, Wells and Lake Streets – has served as the Windy City’s central business district since the city was officially founded in 1833. Not surprisingly, the area has a long and glorious history of watering holes catering to the local working stiff; the Eagle Exchange Tavern, Chicago’s first such establishment, actually opened on Lake Street near Wacker Drive some four years before the city’s founding.

After several decades of decline, during which most Chicagoans wouldn’t have been caught dead in the Loop after dark, the area seen a wealth of shiny new gastropubs, rooftop cocktail bars and other high-end nighttime destinations opening in recent years. But if your taste (like mine) runs to the sort of history-steeped daytime establishments where local workers have been enjoying liquid lunches and frosty five o’clock mugs for longer than you’ve been alive, there are happily several such places still in business. And since they’re all within reasonable walking distance of each other, I thought it would be, er, educational to spend a Friday soaking up the beer and atmosphere of some of the Loop’s oldest remaining saloons, and seeing how they’re adapting to the craft era.

Joining me on my Loop crawl was my lovely wife Katie, and ace photographer Steph Byce, both of whom thankfully dig beer and old-school bars as much as I do.

Steph ByceMaybe get yourself a to-go cup if you're a Lollapalooza punk.

Sky Ride Tap 

Time: 10:20 AM
Location: 105 W. Van Buren Street (Clark Street)
Opened: 1930s

Supposedly named after the most popular attraction at Chicago’s “A Century of Progress” World’s Fair of 1933-34, the Sky Ride sits in the same space under the Van Buren “L” tracks where notorious Chicago power broker Michael “Hinky Dink” Kenna opened his first saloon, Hinky Dink’s Place, back in 1886. In addition to its free lunches (Kenna’s way of currying favor with the local bums, who could then be relied upon to do his bidding at the polls on Election Day) and the illegal gambling den on its second floor, Hinky Dink’s Place was known for its “two-handed schooners” – massive 3 ½-pound glasses filled with 25 ounces of watered-down beer.

These days, there’s nary a trace left of the location’s sordid 19th century past, or even of its 1940s incarnation as a popular piano lounge. Judging by the Sky Ride’s colorful sign (probably the best thing about the place) and Formica-paneled interior, the place underwent a pretty heavy rec-room makeover sometime in the 1970s. The two-handed schooners have long since been replaced by three-dollar bottles of Miller Lite and Miller High Life – which we duly ease into our crawl by ordering – and stacks of Styrofoam “go cups” behind the cash-only register. Not the place to go if you’re looking for any kind of craft beer, in other words, but you can definitely whet your whistle here on the cheap.

The bright fluorescent lighting and haphazardly displayed Black Hawks pennants don’t do much for the atmosphere, but the Sky Ride – which conveniently opens at 7 a.m. – is still a beers-and-shots favorite with workers from the nearby Board of Trade, and is also rumored to have a great jukebox. At this time on a Friday morning, however, there’s only a handful of glum regulars watching The Price Is Right, and an irritable bartender muttering about all “the punks” she had to deal with during Lollapalooza. She’s also giving Steph and I a pretty serious side-eye for taking photos and jotting down notes at the bar, so we quickly drink up and move on.

Steph ByceLook at that dark and beautiful bar.

Kasey’s Tavern

Time: 11:06 AM
Location: 701 S. Dearborn Street (between Harrison and Polk streets)
Opened: 1974

This Printer’s Row fixture is technically located a few blocks outside of the Loop, but it’s a beautiful day for a walk, and we don’t want to miss out on a chance to enjoy a beverage at a bar that claims ownership of Chicago’s second oldest liquor license. While it’s only been Kasey’s since 1974, this space has housed one pub or another since the late 19th century, when the area (then known as The Levee) was chiefly known for its brothels and dance halls, which functioned under the protection of Chicago politicos like “Bathhouse” John Coughlin and the aforementioned Michael “Hinky Dink” Kenna.  

These days, the area is considerably less vice-laden, but Kasey’s still has an appealingly old-world atmosphere, even with a row of flat screens positioned above the gloriously long wooden bar. Maybe it’s the ornate stamped-tin tiles on the ceiling, or the historic Chicago photos lining the wall; or maybe it’s the welcoming tranquility of a barroom lit only by the rays of sun coming through the front windows, or the equally welcoming “Sout’ Side” patter of our bartender – who seems genuinely happy to see us, even though we’ve wandered in a mere six minutes after the place has opened.

Kasey’s has Hamm’s and Carlsberg tall boys on special today (three and four bucks each, respectively), but we’re more interested in choosing from the 35 craft beers they have on tap. Steph goes with a Ghost of ‘Lectricity Kolsch from the local Around the Bend brewery, Katie quenches her thirst with a Schofferhofer Grapefruit Hefeweizen, and I dig into a Double from Chicago’s Old Town Abbey Ales.

A dark, malty and spicy Belgian-inspired beer might seem an odd choice on a warm August morning, but it’s making me very happy right now – as is the overall vibe of this place, even as the bar stools begin to fill up with the lunchtime-drinking crowd. I could easily see myself spending an afternoon here with a good book and a few other selections from Kasey’s draft menu; alas, duty dictates that we must move on.

Steph ByceA little bit of history with your beer.

Exchequer Pub

Time: 11:56 a.m.
Location: 226 S. Wabash Avenue (Jackson Boulevard)
Opened: 1969

The first thing I notice upon arriving at the Exchequer is a Cubs “World Series Champions” banner visible through the front windows. This comes as an amusing surprise to me, since the Exchequer is strictly White Sox territory, as evidenced by the wide array of ChiSox memorabilia hanging throughout the spacious restaurant and pub, as well as the guy a few stools down from us who’s wearing a Jose Abreu jersey. Maybe the banner was hung there to attract tourists, though it mostly seems like locals in here today – folks like the middle-aged dude sitting next to Katie, who tells us that he’d happily do a shot of Malort right now if he didn’t have to get back to the office. (“That’s why I’m only drinking rum and diet coke,” he adds, ruefully.)

Though the Exchequer opened in 1969, there have been bars and restaurants in this place under the Wacker “L” tracks for nearly a century, including the notorious 226 Club speakeasy, one of Al Capone’s favorite joints. Numerous photos of ol’ Scarface are plastered around the joint, while an old “Wanted” poster and a replica (I think) of a 1920s submachine gun hang above the host stand.

I briefly consider ordering an Exchequer Amber (“a specialty American dark lager with a rich, roasted taste”) – but in honor of the federal agent who helped bring Capone to justice, I decide instead on a Great Lakes Eliot Ness lager, one of 17 other beers available “from the faucet,” as their beer menu puts it. We could “Chicago” it up further by ordering the Exchequer’s deep dish pizza, which is supposedly excellent; but not wanting our crawl to be derailed by the need for a post-lunch nap, we opt for some mozzarella sticks, instead.

Katie surreptitiously texts me the message, “Our bartender is totally hungover.” Sure enough, she’s not only obviously still wearing last night’s mascara, but she seems to be having trouble remembering who ordered the Eliot Ness, even though she’s pulled it right in front of me and hasn’t really moved from the same spot since I ordered it. (“Ooh girl, what did you do last night?” we hear a regular ask her.) We drink up and vacate our stools – though not before leaving a nice tip for our bartender, who we’re frankly feeling kind of sorry for. Hey, we’ve all been there, right?

Steph ByceAll the Veeck you could wish to peep.

Miller’s Pub 

Time: 12:52 p.m.
Location: 134 S. Wabash Avenue (Adams Street)
Opened: 1989

A Loop favorite since 1935, Miller’s Pub moved to its current location in 1989, but the owners thankfully made every attempt to reproduce the clubby, comfortable look and feel of the original in their newer, larger space. (“Just the right amount of old school,” brags the establishment’s website, and that’s not an inaccurate description.) Unlike its neighbor, the Exchequer, Miller’s seems to be doing a booming business today with tourists, many of whom are arriving for lunch in large family groups.

Happily, this means that there’s plenty of room for us in Miller’s often-packed bar – specifically in the holy shrine by the windows known as “Bill Veeck’s Corner,” which is stacked nearly to the ceiling with framed photos of the two-time White Sox owner (an all-time hero of mine) and other Comiskey Park luminaries.

The irrepressible Veeck was a fixture at the original Miller’s location, where he would often stop for a drink or three after shopping at the nearby Kroch’s and Brentano’s bookstore, and amuse those around him by stubbing out cigarettes in a special ashtray that had been built into his wooden peg leg. But while “Sports Shirt Bill” was a Blatz man, it’s not one of the 23 beers on Miller’s tap list, so I toast his memory with a thirst-quenching Metropolitan Krankshaft, insted.

We’re almost all the way to the next stop of our crawl when I realize that I’ve left my phone at Miller’s. In a panic – it’s foolhardy to leave your phone unguarded in downtown Chicago for even a minute – I run (okay, maybe race-walk) all the way back, fully expecting it to be long gone by the time I get there. But as soon as I walk through the door, I see it still sitting there amid our empty glasses in Bill Veeck’s Corner, miraculously untouched.

Good lookin’ out, Bill!

Steph ByceThe view from downstairs.

The Berghoff 

Time: 1:45 p.m.
Location: 17 W. Adams Street (between State and Dearborn streets)
Opened: 1898

A truly iconic Chicago establishment, the Berghoff restaurant has been serving up heaping helpings of reasonably-priced German food since the McKinley Administration. It’s also home to one of the most gorgeous drinking spaces in the city, with its long, sinuously curving wooden bar, an ancient-looking wooden clock, brass railings, ornate light fixtures and faux-medieval murals.

Unfortunately, said bar turns out to be currently under renovation, so we’re guided instead to the dubiously named “pop-up speakeasy” located in the restaurant’s basement, a small room with same oak paneling of the upstairs bar but little of its charm. It feels a little like piling into a VW Bug after expecting to be picked up by a Rolls-Royce limo, but at least there are three empty stools left at the bar. “The bar upstairs is gonna be beautiful when it’s done,” our bartender assures a regular, and possibly herself. “But this place is cute, right?”

The first Chicago establishment to be granted a liquor license following the repeal of prohibition, the Berghoff originally opened as a venue for founder Herman Joseph Berghoff’s Dortmunder-style beer, which was apparently quite a hit at the Chicago World’s Fair of 1893. (The restaurant’s main dining rooms feature stunning murals of the opulent neo-classical “White City” built for the fair.) The speakeasy offers three Berghoff beers on tap – Original Lager, Hefe-Weizen and Dark – along with Krombacher Pilsner. I opt for a mug of the Dark, a solid-if-unremarkable dark lager that pairs very nicely with the plate of pierogis and the manhole-sized soft pretzel that we order to soak up the day’s libations.

Steph ByceYep, looks like it serves Belgian beer and has comfortable seats. Checks out.

Monk’s Pub 

Time: 3:40 p.m.
Location: 205 W. Lake Street (Wells Street)
Opened: 1969

It takes Katie, Steph, and I about twenty minutes to walk from the Berghoff to Monk’s, but it feels good to move around after all those German carbs, especially knowing that we’ve got to make room for some Belgian ones. Located in the shade of the Lake Street “L” tracks, just a block or so from where the Eagle Exchange Tavern once stood, Monk’s originally opened on Lower Wacker Drive in 1969, and moved to its present address in 1971; the “monastic” look of its interior and exterior are the result of a 1978 makeover.

I haven’t been to Monk’s since the summer of 1982, when some older co-workers dragged my teenaged self along for a post-work beer. (Nobody bothered to card me, even though I looked about 12.) Within less than a minute of grabbing a stool and getting an eyeful the place’s “olde world” charm, I find myself lamenting to Katie that it’s been so long since my last visit.

The dark wood bar, the exposed brick walls, the peanut shells on the floor, the shelves filled with old books, the vintage 70s Tiffany-style Schlitz lamps – and did I mention a beer list with 16 on tap, 55 in cans, and 120 (mostly Belgian) in bottles? As I scan the menu, my eyes bug out like I’m in a Tex Avery cartoon; and by odd coincidence, the Avery Brewing Company is doing a tap takeover at Monk’s this week. Still, I’ll always go Belgian if given the chance, so I order a Bosteels Pauwel Kwak, which tastes just right in this well-worn setting.

This Friday afternoon, Monk’s is doing a bustling business this afternoon with folks from nearby offices who are getting an early start on their weekend. And while we haven’t exactly put in what most people would think of as a “hard day’s work,” this really does feel like the perfect place to kick back and celebrate the end of our crawl. And yes, I will have another beer…

“I want you to feel like this place is your Cheers,” our friendly bartender informs us while pouring my Westmalle Dubbel into a waiting goblet. Sure, that sounds kind of cheesy; but if I were lucky enough to work in the vicinity of Monk’s, everyone here would damn sure know my name.    

ZX Ventures, a division within AB InBev, is an investor in October
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