A Chicago Bar Crawl in Search of Old Style and Authenticity

Have you ever been driving north down Milwaukee Avenue and noticed that the moment you pass the Logan Square Blue Line stop, there is an abrupt absence of young white people: so abrupt, in fact, it feels like there’s some sort of invisible forcefield, as if the music of Vampire Weekend simply bounces back into the atmosphere, rendering anything north of Kedzie totally unliveable?

Today’s hipsters move to Chicago in search of authenticity. But here’s the thing: they limit themselves to certain neighborhoods to such an extent that they never allow themselves to see the real, salt-of-the-earth city made famous by Algren and Royko and Dybek.

So, in the name of cultural ambassadorhood, Dispatches From the Northwest Side has created a Milwaukee Avenue bar crawl itinerary for those in search of a real Chicago experience. It begins north of Addison and takes you all the way to Devon, farther and farther from the hipster center of Logan Square. If you go with an open mind, don’t be surprised if you find yourself, by your third or fourth Old Style, having an actual, earnest, unironic good time.

Kennedy’s—3734 N. Milwaukee Pat Kennedy, from Co. Clare, Ireland, is the quintessential bartender—he knows a little bit about everything. There is nothing about Chicago politics or sports that he can’t discuss. And if you can ignore the fact that this place is on an abandoned strip of Milwaukee Avenue, just below the Grayland Metra station, has no name on the front, and looks disturbingly similar to the bar in Mystic River where Sean Penn shootsTim Robbins in the face, you will be pleasantly surprised. The bathrooms are clean. The jukebox rules. The Guinness is three dollars a pint.
Best overheard quote during the Chicago Teacher’s Strike: “I’d take that Karen Lewis broad more seriously if she didn’t wear her hair in ‘dose crazy corntails!”

kennedy's pub

The Windsor Tavern—4530 N. Milwaukee Avenue  This little place has surprisingly good quesadillas, a nice beer garden, friendly regulars, and a religiously devoted group of Bears fans.
Best quote overheard circa 2005: “’Ey Bill! Didja see that homo cowboy movie?”


The Capitol Night Club—4244 N. Milwaukee Avenue  I have a Czech friend  who once demanded to know why Americans always smile in photographs. “Why do you have to show all your teeth like that?” she asked. “You’re not really that happy, and you know it!” It’s this distinctly Eastern European dark worldview that makes me love the Capitol Club. Although it is awash in neon and stripper poles and populated by the young and beautiful of the Northwest Side’s Polish community, the bar has a post-Communist air to it, a hangover of suffering and privation. Here you will drink and you will dance, but all with a trudging purpose, and never forgetting the futility and ultimate darkness of human existence. You won’t fit in here, and unless you are tall, blonde, Slavic, and wearing six-inch heels, no one will talk to you. And that is as it should be.

Fischman’s Liquor—4780 N. Milwaukee Avenue At this point, you are realizing you have crossed into the Hinterlands. There is no Urban Outfitters for miles around, the CVS across the street doesn’t even sell mustache wax, and you are going to be thirsting for a reminder of your former life. Fischman’s, with its selection of craft beers and Thursday night food trucks, will return you to a place of hipster equilibrium. You will still probably get stared at, though.
Best overheard quote: “Malort dis guy’s ass—NOW!”


Zachary’s—5368 N Milwaukee Avenue  Generally, I avoid bars with wall-to-wall carpeting. But how can you go wrong at a place that provides plastic seating out front that looks ripped out of a Greyhound station? And that’s open til 5 a.m.? Actually, on second thought, you might want to save this place for the very end of your bar crawl. I’ve never been here before 2 a.m. and can’t vouch for its safety before the late night crowd arrives.


The Thatch--5707  N. Milwaukee Avenue If you come here, you will be the only American in the place. But if you tip well, behave yourself, and buy a drink for the person sitting next to you, the Irish who hang out here might choose to accept you.

the thatch

Three Counties--5856 N. Milwaukee Avenue My favorite part of this bar is the little beer garden out back, which is usually filled with old men in gleaming white gym shoes and nylon jackets, leaning together smoking cigarettes and talking Cubs baseball.

3 counties

Jet’s Public House—6148 N. Milwaukee  Since this bar is full of alpha males in sweatpants, it’s no surprise that there’s no better place to watch a Hawks game.
Overheard quote: “Can I get the cheese basket, hun? But instead of the curds, can I double up on the mac n’ cheese bites?”


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