UPchicago Bar Crawl: Wicker Park

Wicker Park is home to countless galleries, boutiques, restaurants, and bars that promise a little something different than any other part of the city. This neighborhood has completely transformed over the past 10 years and is constantly changing to keep up with the trends and people who inhabit its streets. As it caters to a wide variety of interests, it would be a challenge not to find your niche in Wicker Park.

Neighborhood bar crawls are becoming second nature to us. This time we set out without even having an exact plan, knowing that Wicker Park has a plethora of nightlife spots just waiting for us to explore. There are so many bars centered around the North Avenue, Milwaukee, and Damen intersection, you could certainly create several different crawls, but here’s one we know will guarantee a great night. You’ll truly understand the range of bars that exist in that area and leave with a true taste of Wicker Park.

The plan? Meet at Beachwood Inn, and crawl our way through the night to whatever bars sound most enticing. The results are in…

Beachwood Inn — Cheryl Thomas
1415 N. Wood Street

I entered the dimly lit Beachwood Inn in Wicker Park around 7:30 p.m. It was bar number one on our crawl, and it’s a good thing we chose Tuesday — Bell’s is on special for $3.50. Yeah!

Since its opening in 1950, Beachwood Inn has been a unique retreat from the more trafficked bars in the neighborhood. If you’re set for a long night here with a group, grab a seat in one of the two booths in the corner close to the jukebox or at a table along the wall. I spotted a stack of board games in the back — Clue and Connect Four! On the other side of the room is an old-school pinball machine, Rescue 911 nestled in the corner by the pool table.

Chicago sports flags pepper the walls between movie posters and illuminated beer advertisements. Even Cubs and Sox memorabilia live in harmony (what!?) on the back wall, something unheard of in North Side or South Side dives. The checkered ceiling, which is painted an otherwise hideous green, reveals the remains of a typical historic Wicker Park building.

And of course the most important thing to mention. Drinks! They’ve got a nice selection of bottled beers. Domestics run around $3.75, imports at $4.75. Two things to keep in mind: it’s cash only, and the only food you’ll find is Vitner’s Potato Chips. So, it’s not the place if you’re hungry for some bar grub. But it’s the perfect spot to sip a Guiness, lip-sync a Rod Stewart song, and dominate a friend in Connect Four.

Subterranean — Gene Wagendorf III
2011 W. North Ave

What trounce through Wicker Park would be complete without some live music? Not one that I want to be a part of. On the evening of this particular bar crawl the stars seemed to be aligned for us UPchicagoans: one of our writers, Andrew, had a previously canceled gig rescheduled at SubT for the very night that we’d be staggering around the area.

Subterranean is perfectly positioned right next door to Estelle’s, which makes it damn near impossible to end your night early, not that I’m complaining. Covers tend to be on the cheaper side for weeknight shows ($8 to see the gloriously New Order-esque Moon Furies) and the bar has a nice mix of super affordable beers and decent micros. The checkerboard main floor has excellent sight-lines and good sound, but the best place to take in a show is from the second floor. The front of the balcony has a direct line to the stage and a small bar tucked right behind it. At any moment you’re 180° from either booze or the show. Can’t beat that.

While weeknight crowds for local acts can be a little sparse, Subterranean does get rowdy. I remember seeing Gogol Bordello here in ’04 and thinking the whole place would bust open at the seams, spilling drunk punks out onto North Avenue. That didn’t happen, of course, but it could have.

Moon Furies eventually wound their set down, we finished our beers and began to negotiate the staircase down to street level. After all, there was drinking to do elsewhere.

Salud Tequila Lounge — Phil Kranyak
1471 N. Milwaukee Ave

We are bathed in flickering darkness upon entering Salud. The cozy, semi-circular booths glowing by candlelight, but I feel as if we are convening by torchlight. I had wanted to make a choice of bar that took me out of my expectations, and Salud fit the bill. It’s a niche that I could do with more of: a tequila lounge decorated with as much flavor and variety as is offered in their menu. Everywhere you look is ornate decoration and fine detail. The bar itself is a spectacle to behold; recessed alcoves in the wall hold bottles of choice Mexican gold like archeological treasures.

Salud is no dive bar. To compliment el ambiente grande is a healthy, but not overdone, selection of tapas and specialties. We were there mostly for the drinks, but I had a good long look at the food and have a date with the red snapper filet in the near future. The drink menu is also very modest yet appropriate. I always feel slightly disarmed and concerned when a menu of food or drink spills onto pages past where it should. If you could do one thing well, would you need to do forty? Thankfully, Salud gives you enough variety to keep you coming back without making you wonder if any of it will be worth it.

And it is worth it. We try a selection of margaritas that are all superb. Gene and I are barely pulled away from sampling straight shots of different tequila. We told ourselves we had to move on; likely it’s because the selection is so compelling that we didn’t think we’d be able to stop. They also have a rum menu, and since several items are advertised as ginger-infused, I may also have to add one of those to the mix. We cannot stay forever, and as it is with so many things in life, when we must depart from Salud it’s difficult to say goodbye.

Gunners — Tessa McLean
1467 N. Milwaukee Ave

Gunners is a creation of greatness. Brothers Eric Palm of 14 years of Matchbox fame and Dan Palm of Silver Palm came together to create this small bar, emphasizing the importance of classic cocktails and good, simple food. In fact, simply calling it a bar seems almost an insult.

If you’re heading to Gunners, be prepared to enjoy a classic cocktail. Sure, you could order a vodka soda or a PBR (it is Wicker Park after all — and yes, many of our writers did partake in this tradition). But a good cocktail is what they do best. When was the last time you heard someone order a Gimlet or a Sidecar? It may have been awhile, but they’re delicious, if somewhat outdated in terms of the trendiness of mixology these days. I opted for a margarita because I am a sucker for margaritas served like martinis. A margarita on the rocks has its purpose, and don’t even get me started on that frozen crap, but a well-chilled margarita with the right ingredients served up in a martini glass is a thing of beauty. They do a lot of their martinis with a sugar rim, which isn’t my favorite, but is certainly a nice touch.

The main menu is short, but incorporating bar favorites with little twists and spins all over the place. Three Floyd’s beer battering enhances typical onion rings and chicken tenders, and many menu items come served with house-made sauces. Mini chorizo tacos with just the slightest hint of pineapple topped with pico de gallo were a delicious steal at $1 a piece on Tuesdays. And since we left I’ve been thinking of returning to try the Hog’s Boss.

Gunners is certainly worth a stop in the diverse bar world of Wicker Park. The dark wood paneling will transport you to a time of simple cocktails and intimate conversation. But we’re slowing down and it’s time for one last spot…

Estelle’s — Jackie Berkery
2013 W. North Ave

Ah, Estelle’s. The perfect nightcap. This decidedly unpretentious bar and lounge plays great rock music and draws a fun mix of people. The atmosphere is low-key and relaxed, even into the wee hours of the morning. If you wanna give those dancing shoes some exercise, this may not be the spot for you. But if you’re up for hanging with a good crowd and drinking even better beer, Estelle’s is where it’s at. The awesome beer list includes several Three Floyds brews as well as many other microbrew craft breweries. But don’t worry, you PBR and Bud Light drinkers, they’ve got that, too.

With a fabulous jukebox and its art deco decor, the bar gives off a nostalgic feel. A friend of mine described it as “diner-meets-euro-grunge.” Contemplate that. If for nothing else, come here for the excellent service and extremely friendly and personable bartenders and staff. That’s not something you’ll find everywhere in the neighborhood, and it’s certainly refreshing. Alas, the night is winding down, a few of us have had one too many drinks, and it is a Tuesday, after all. As we part was and bid adieu to Estelle’s, I’m certain it won’t be long before I’m back again.

Another day, another crawl. Gotta love this “job.”

Map it:


Wicker Park Bar Crawl in a larger map

About UPchicago Team

Urban Philosophy is a way of thinking that you develop when you’re a true city person. Whether you’ve spent your whole life living in Manhattan, or you just moved from small-town Iowa to the city of Chicago, the longer you stay, the more you come to understand what it means to live in a city. Our Urban Philosophy is that no matter who you are, where you are from, and what your likes and dislikes may be, there’s something for everyone in city life.

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