Estelle's ChicagoNot to be confused with Estelle’s Pub on Devon, Estelle’s Cafe & Pub has catered to a diverse drinking base in Wicker Park since 1988 and has since become a neighborhood original. Once a seedy dive, Estelle’s has recently been renovated into a stylish bar that, although a far cry from its predecessor, continues to fit in well with the area. Open-mic nights and drink specials attract regulars during the week while late-night burgers with cocktails attracts everyone on the weekends. While rather small in size, Estelle’s reputation is growing and, if you’ve never heard of it before, read on as you may have just found yourself a new favorite spot west of the Kennedy.

Estelle’s Cafe & Pub is located within eyeshot of the Milwaukee, North and Damen intersection dominated by the flatiron Coyote building. Here it has been since a woman named Estelle fronted the money to transform the bar that briefly inhabited the establishment before it, known as Adolph’s, into something more appealing. Today, with its humble orange neon sign glowing above a blue awning with white Art Deco lettering and a facade with glass blocks and plate glass windows, Estelle’s can be easily missed. Just look for its neighbor, Subterranean, and walk one door west.

Estelle's LadiesWhile Estelle’s looks quite dark from the outside, step through the modest plate glass front door and you’ll find a swanky yet classic Chicago imbibery inside. The room is lit in a bluish-green glow inside, dominated by an interestingly-shaped, long wooden bar runs along the east wall. The middle part of the bar juts out into the room, accommodating the grill behind it and making it rather easy to order a drink (unless the bartenders are preoccupied with playing their own CDs). The bar itself actually dates back to the 1930’s, when Estelle’s was known as the Tower Lounge and live music acts played behind the bar where the grill now stands. Purple beveled glass lights behind Kelsey’s-like mirrored glass shelving complement the recessed blue-green ceiling lights that somehow light the whole room. Darkened televisions lie in the corners, providing entertainment for those that get bored with the local artwork exhibited on the maroon and orange-painted walls across from the bar.

      • Estelle's Interior
      • Estelle's Booths
      • Estelle's Bar

    “When the new Estelle’s opened its doors nearly two years ago, there was a steady stream of displaced junkies wondering what the hell had happened to the old Estelle’s.”

    Shecky’s Bar, Club & Lounge Guide 2002

    Estelle's LassesA trendy crowd like that which hangs nearby Holiday Club, Double Door and Northside head over to Estelle’s afterwards for late-night cocktail action as well as the kitchen, which makes Estelle’s one of the only bars I know of that serves food until the wee hours. In this way, Estelle’s is like a cross between Nick’s Uptown and Marie’s Riptide for ambience and the Beat Kitchen and Fireside Restaurant & Lounge for late-night dining. In 1999, Estelle’s underwent a serious renovation and the crowd followed suit. Previously, Estelle’s regulars could best be described as, “The rejects of society, drinking, shooting pool, and ready to rip your hair out if you don’t look like them,” according to one Metromix reviewer known as “cooper.” Between 7:00 p.m. (when the bar officially opens) and 2:00 a.m., as well as during a spate of time recently when they had their liquor license temporarily revoked, Estelle’s can be pretty dead on the weekends. However, as it was prior to renovations, Estelle’s attracts a die-hard, Bohemian local crowd of artists, musicians and newcomer internet techies from Sunday through Thursday. At these times, the true flavor of Estelle’s can be experienced and is when owner Ben Klop is most happy of his creation. Special note: if you do a web search for Estelle’s, you may find that it turns up on many LGBTQ+ friendly bar listings for Chicago. From my experience, this couldn’t be further from the truth. Perhaps Estelle’s once may have attracted the LGBTQ+ but doesn’t appear to do so today.

    “Hard to believe this late-night standby was a total shithole before 1999 renovations.”

    – strong words from a normally docile Official Chicago Bar Guide (2001)

    Estelle's Open-MicPatrons take a load off at a plethora of stools along the bar or in leather booths along the south side of the room, while listening to music from Built to Spill, Rolling Stones, Yo La Tengo, Beastie Boys, Chuck Berry, and Johnny Cash on what Estelle’s staff (like every other bar in Wicker Park) considers the best jukebox in the city. All of this even inspired a Chicago Bar Project fan to submit a story, written in Kerouac “kickwriting style” (see below).

    In-between games of pool on the red-felted table on which a patron would occasionally vomit in the old days, today’s hungry horde takes advantage of “the best burgers in Wicker Park” up until 4:00 a.m. Other fare, including steak, tuna wasabi, and, allegedly, pasta dishes supplement Wimpy’s favorite. Though these menu items are not consistently available, rest assured that they’ll make you whatever they have. Food from Sorrev’s, a gyros joint around the corner, used to be available but, sadly, is no longer there.

    Estelle's BartenderBack in the day, part of Estelle’s initial appeal to patrons was that it was home to the Wicker Park Poetry Project and The Shappening, much in the tradition of the Green Mill, Weeds and Gold Star Bar. The Wicker Park Poetry Project was named by host Kristen Shout, who took over the tradition from Jose Chavez and hosted it from 1990 to 1992. During that time, Shout was also on the Chicago Poetry Slam team in 1991, which was the last time that the Chicago team won the National Slam. Kristen then passed the torch to Thax Douglas (of Lounge Ax fame), followed by Dave Gecic and, The Shappening. The latter was a popular, free, open-mic slam poetry event hosted by “Shappy” every Tuesday night from 10:00pm to 1:00am Shappy once performed at Lollapalooza and on Comedy Central and, as part of an evening with Shappy, slam poets espouse with a musical background consisting of drums, bass and flute, known as “The Shappening Band.” It is not clear whether slam poetry hosted by Shappy is still going on at Estelle’s, so I recommend you give them a call to get the latest update before you head over there to express your anxieties.

    As partly evidenced by the fact that they never has a cover or a dress code, Estelle’s is a great Wicker Park neighborhood joint – one step up from the likes of Lottie’s Pub, Lemming’s and even Nick’s. Head over to Estelle’s for some slam poetry or a chat with the regulars during the week, or a burger and a cocktail late-night on the weekends. Who knows, you might just meet a “friend” in the process. For more information, check out the Estelle’s website. Umm, hmm…

    “This is the place your mother warned you about”

    Of Cloves and Water Bras by George K.

    Once, at a stupid night at Estelle’s, too young to completely understand Chicago’s bar scene, I was hanging out with this group of girls my friend had met the week before at Lava Lounge. So, we were back there and where else does somebody go but Estelle’s after hours. I think I had on some light green Urban Outfitters big-collared thrift-looking number on, and I had just given myself a personally-done crew cut over the tub at home, so I was looking pretty Wicker-alterno besides the accompanying suburbo-Gap carpenter pants to go with it. But aside from that and the fact that the garb didn’t exactly compliment my dark Mediterranean features (why was I trying to be a light-skinned alterno Michael Stipe dude?) I was looking pretty un-poseur-ish, at least until my hair grew out. So we’re at Lava Lounge, in the back room; that annoyingly intimate dorm-looking room, with the painted walls and comfy couches, and I was feeling pretty swank having downed a couple at home before I made my arrival where these group of girls were just waiting for me. I made a pretty confident entrance, and I pretty much just sat next to the first girl who had an available seat next to her. We ended up talking the rest of the night and she was ripping on her friend’s 15th dye job in the past year, and she had this totally conservative orange-shirt that I later found out once we were a couple that she complimented with a water bra (how fair is that?), so in the totally desperate, immature way of doing things we designated each other to ourselves with those humiliating, but electrifying signals like excusing yourself to go to the bathroom, politely involving the other person in any conversation, you know, all those thrilling things that happen when you know it’s you and that other person and nobody else, and you know that you’re too scared to keep your options open, no matter how obvious or how rational or good-looking the other options might be.

    So after Lava Lounge we were all feeling pretty good about ourselves, and even though we weren’t in the suburbs, we felt fairly safe to not be ultra-urban-hip since Lava makes everybody feel at home (and there was even a wedding party that stumbled in towards the end that I am forever grateful for that looked more out of place than anyone there), so we decided to go to an after-hours place, which ended up being Estelle’s. We must have gotten there before the influx of people because somehow we got a booth and I’m really hopping in my seat and my friend’s continuing his wooing of my friend’s friend and I’m at this point not even paying attention to anything in this place except this girl, which probably isn’t a good thing to do cuz then you have nothing if she leaves but I was never good at multitasking and it felt right, so who cares, right? Then, of course, I’m smoking, which she likes to do on occasion but she isn’t a ‘smoker’ per se, and I know that she isn’t because of how she is and who she is and that must make me the devil so I without any reluctance assume that role, and I ask for one of her friend’s clove cigarettes. And I’ve never really gotten over the comradeship and youthful rebellion thing that attracted me to smoking so I’m using it as our connecting point–I want her to smoke like crazy and she knows it, I want to be able to share that with her and she knows it, because every fun, stupid night-life thing I did in high school and college involved smoking, it involved the stupid close feeling you have with people when you ask, “dude, can I borrow your lighter?” And they say, “sure, man”, slowly handing you the lighter with some kind of holiness that we must have equated from all the rites in church that have to do with lights–candles, incense, etc. But now we have the most holiness of tobaccos, the one thing that resembles church and all that is holy that I perceive myself as a holy smoker, absolved from all the condemning anti-smoking 20th century PR campaigns: we have clove cigarettes. With their blackness and their sharp, crackling aura, their holiness will absolve me of my late-night skirt-chasing, beer driving, evil big city night train rides. So I get one from her friend and light it up with same reverence that I did in high school, when there wasn’t beer yet, and at this point I’m so confident in myself and feeling so ripe and so attached to this girl that I can do anything. I feel like I’m in a movie, and all reality is whisked away, and I’m thinking I have to be some movie star for this girl so I’m delivering cheesiness and acting strange and unpredictable and trying to take her away from her crappy reality, and we’re not talking about anything anymore because we’re both tired of normal conversation. We’re at Estelle’s, in Chicago’s hippest neighborhood, and we’re getting away with acting like 2 seasoned urbanites, socialites, trendites, etc., and whether or not we actually are, as far as we’re concerned we are–it didn’t matter what the crowd thought–we both felt it. So I comment to her that you can taste the clove on your lips after taking a drag. I am so enamored with the mystical separation smoking gives you from the non-smoking outsiders. I comment on the clove taste after taking a drag, and I ask her to take a drag, which she probably had already since we were probably sharing the cigarette in our little enclave of ecstasy, so she takes a drag and I want to see if I can taste it on her lips too, so I kiss her. I kiss her to see if I can taste the clove on her lips. I have successfully entwined smoking with kissing. I have successfully entwined the holiness of incense with this girl. This is too much, and she’s just going along with all of it and having a great time. I am so surprised, I cannot believe it.

    For the next eight months, she brought this up all the time–and she chose Estelle’s as the bar to go to for her birthday a few months later. She told everybody this is the bar where we first kissed. And then she told the story of how it happened and it probably disgusted some people. But who cares, right, that’s what going out on the town is for, right? To act like an idiot in public. To make yourself more high profile. I was definitely never more high profile than I was back then. A city dweller, an urban rocker. Just call me Nash Kato.

    And she eventually confessed to me that she was wearing a water bra that night. So she fooled me and I fooled her. The feeling was mutual. But I did get her to smoke more which is something I can be proud of. Because it’s such a holy thing.

    – George K.