UPchicago Bar Crawl: Logan Square

It’s that time again. Bar-crawling time. Thanks to the success of our first attempt at this new project, we all rallied again for boozing and “research” — this time in Logan Square.

Unlike its west side neighbors, Wicker Park and Bucktown, Logan Square hasn’t experienced as much gentrification and influx of upscale businesses. Instead, the neighborhood has transformed into what its counterparts used to be: an up-and-coming area filled with young residents who moved from the more pricey areas of Lakeview and Wicker Park. Interestingly enough, though, the influx of new, energetic residents hasn’t brought the onslaught of restaurants, bars, and galleries… yet. For now, Logan Square remains a fairly under-the-radar place to live, with minimal attractions but a cool vibe and friendly inhabitants. So, we made it our mission to check out its top spots — and trust us, there are some good ones.

The time: 7:30. The place: The Boiler Room. The only instructions: come with your drinking shoes on. So, we gathered, all fairly jovial that our job includes research that consists of beers and bar food. And here’s how it went:

The Boiler Room — Tessa McLean
2210 N. California Ave.

As a big fan of Simone’s in Pilsen, I was excited when I heard the owners were opening a new spot in Logan Square. If the decor, food, and beer selection was even half as good as Simone’s I knew this would be a great place to make our first stop on our Logan Square bar crawl. One of the things I love most about Simone’s is the innovative decor, a bar built from salvaged pinball machines and an old bowling alley, and the Boiler Room may even beat it, if even simply based on awesome bathrooms. That’s right, I loved their bathrooms! Enter though an old “L” train door and another one to enter the stall, and experience what it is like to pop a squat on the blue line. The experience is authenticated even more by a soundtrack exclaiming you are on a blue line train heading toward Forest Park. As you exit, “Ding dong. Doors closing.” The male patrons of our crawl couldn’t have been more excited about the safety straps located above the urinals. But enough about the bathrooms. The rest of the bar is made from scrapped metal (the lighting) and old school desks and cargo straps (tables and chairs). They even have a nice, albeit no frills, patio out back with ample picnic tables.

And finally, our first cocktail. With our group it was a surprise everyone skipped the beer list and went for the enticing cocktail menu. Collectively, we tried the Ginger Snap Sap, the 1988, the North Sider, the Toy Gun, and the Hum Fizz, and not one of us was disappointed. The 1988 (rum chata, van gogh espresso vodka, and absolut vanilla) is served with a side of cinnamon toast crunch. What’s not to love? Oh yeah, and they have Jameson on tap. Dangerous. Though it goes perfect with what I call the hipster special, a shot of jameson, a PBR, and a slice of pizza for $7.

As it was our first stop, we needed to fuel up with some food in order to make it though the night. We ordered a “Logan” pizza, which came with mole sauce, fried onions, chihuahua cheese, and pulled pork. It also came with what I’m still convinced were roasted pumpkin seeds, but our waitress (who was pretty awesome by the way) claimed were pine nuts. Probably a good thing to include on the menu in case people are allergic, but luckily we are a food-allergy free crowd. Anyway, the out-of-the-ordinary pizza was delicious and perfect to split between five people. The pizzas come by the slice or whole — and whole means big and filling, especially when the ingredients are so substantial. With food in our bellies and a drink (or two) put away, we were on to the next stop.

Cole’s Bar — David Frankel McLean
2338 N. Milwaukee Ave.

Cole’s was by far the most relaxed establishment to house our crew that evening, and everyone took the opportunity to stretch out and do their own thing. It’d be a mistake to call this place a dive. Rather, its laissez-faire attitude and dark interior is quintessential Logan Square. This place is known for sporting local bands that fill the back room with no cover; but with no music this night outside the traditional jukebox, the lack of TV’s and food made for good conversation.

I chatted up some friendly locals at the bar while petting their dog, choosing North Coast’s Old Rasputin mostly because I’m a sucker for a Nitro Tap (often used with stouts as it creates more head). Their beer selection was small but quality, distinguishing themselves once more from the hipster proletariat snobs who think you’re a douche if you order a beer that costs more then three bucks. Speaking of which, here comes the bike messengers as they file in and watch Phil dance around the pool table like sharks eyeing a dolphin. I’m happy for the distraction as I can’t stop staring at the abortion painting on the wall. They must be true art lovers to put something so morbidly engaging front and center. I get the sense this place will fill up the later it gets, as if the vamps are waiting for the office schmucks to go to bed already. Indeed, it’s putting me in a sleepy mood that would later be jarred awake by the Whistler. This is ironic as Cole’s gets quite lively on the weekends, a friendly watering hole one day and a jaunty music venue the next. As the more gentrified establishments keep creeping up Milwaukee Ave. I’m happy we paid a visit to a bar with Logan roots. Hang in there Cole’s.

The Whistler — Phil Kranyak
2421 N. Milwaukee Ave.

The first thing you notice about The Whistler is that you’ve walked past it. We backtracked until we found a small picture window full of art and an awning carrying nothing more than an address. The bouncer was a friendly young gentleman about my size, meaning that he’d have a hard time bouncing a check let alone a rambunctious patron. I understood as we got inside, however; The Whistler reads like an exclusive New York music nook, only nobody looks at you funny. Everyone we met there, bouncer, bartenders, band, and even a lively, dancing patron were warm and congenial. The Whistler is small, so they don’t beat around the bush— they fill the bush with bourbon. Heavens to Betsy, so much bourbon! My heart sank for a moment. I’ve always stylized myself as a gin/rum kind of guy. I decided to bite the bullet and order a bourbon, no mixer, warm, like a man. To add to the experience I chose Old Grand-Dad, a one hundred proof bourbon. I knew it was one hundred proof because The Whistler lists the proof of each of their liquors. I challenge a corporate chain like McDonalds to print the calories right on the menu next to each item.

My fear about drinking bourbon melted away as I began to sip and the band slipped into their set. Oh, hadn’t I mentioned? The front of The Whistler is taken up by a stage bathed in red light and was home to Darts & Arrows on this particular evening. I’m not sure what genre you’d put them into (as I was drinking one hundred proof bourbon), but they had an upright bassist, so I was pleased as pumpernickel. The final unmentioned feature of The Whistler is the patio. It looks as if your friend from college wanted to have a get-together in his backyard. There are white holiday lights strung around and several table and chair sets. Like the inside of the Whistler, it is small, cozy and inviting. There are some bars where you are trying to have a “blast,” and then there are bars where you go to have a great night; The Whistler is the latter, in every positive sense of the phrase.

Alright, fine, it was an Old Grand-Dad and ginger ale. And I let most of the ice melt into it.

The Rocking Horse — Caitlin Fitzgibbons
2535 N. Milwaukee Ave.

Located right off of the square on Milwaukee, The Rocking Horse is a bar that aims to please. A large rocking horse hangs outside of the bar — a glimpse of the unique decor inside the drinking establishment. The term drinking establishment, which sounds formal and entitled, has been utilized here to make me feel better about being at my 4th of five bars on a Tuesday night.

The interior is lit with small groupings of vintage lighting that look like they were carefully selected at Salvage One. The drink menu offers its hipster clientele a large selection of beers. The Rocking Horse has 16 beers on tap and over 60 types of bottles. I ordered a Three Floyds Gumballhead, which they were out of, so I ended up drinking an ice water. I guess I just got stubborn they were out of my select, because clearly there were plenty of options.

I did sample a bit of the bar fare at Rocking Horse which was delicious. The menu has typical bar food with some unique items like Jalapeno hummus and Portobello fries. We had to go for the regular fries because they make them so many delicious ways. Do you like your fries with gravy? Do you like your fries Greek style? Do your like your fries topped with chili cheese? Maybe you like them chimichurri style? We went for the poutine fries and they did not disappoint. It’s amazing to me how something that looks so inedible because it is covered in brown sauce is actually a heavenly platter of god food.

The bar has plenty of specials — one for every day in fact. If you’re on a date there and you get bored they have games in the back like pool and Pac-Man, so you can feign interest in your date and channel all your energy into the left corner pocket or gobbling up cherries and avoiding blue ghosts. For the good dates that you want to remember forever, you can step into the vintage photo booth and get your picture on.

My only regret of the evening was not looking at the jukebox until I was on my way out the door. I think a jukebox can say a lot about an establishment; a well-balanced selection is key. Walking over to check out the list at Rocking Horse I could have guessed they would have The Smiths and I was correct. The jukebox summed up Rocking Horse for me. They had their classics covered saying “we know our music” — The Smiths, The Velvet Underground, Talking Heads, Sam Cooke, Johnny Cash — but then they’ve got the new stuff to say they’re also hip. In short, what you might find at Pitchfork and Lollapalooza — Pavement, Sleigh Bells, MGMT, Phoenix, Santogold, and Grizzly Bear.

You know what? I think I’ll probably go back. But for now, it’s on to our last stop.

The Whirlaway Lounge — Jackie Berkery
3224 W. Fullerton Ave.

Don’t let the name fool you, the Whirlaway is not exactly what you might expect from a place that dubs itself a ‘lounge.’ This, my friends, is a dive bar. (Of course, in only the most positive sense of the word.) The place is nothing fancy, but that’s part of its charm. You’re not gonna find any local craft beer flowing here, but it’s not that kind of place anyway. In fact, the bar doesn’t have any beer on tap, but fear not: there are plenty of bottles to choose from (over 40, in fact), and domestics are just $2.50 every night. Most of us went with the quintessential Midwest dive bar beer, a good old-fashioned bottle of PBR.

Once we had our beers in hand, it was time to stake out a spot and settle in for our last bar of the night. And that’s when I saw the bookcase — stocked with not only an interesting array of books, but also a mountain of board games. Scrabble, Connect Four, Boggle… they were all there and ready for the choosing, likely depending on your group’s intoxication level. There’s nothing like ending a night with a good game of Apples to Apples, so we went for the classic and snagged a spot at one of the few small tables in the bar.

The Whirlaway has been around for quite some time, and has been family-run since 1980. It’s definitely a “mom ‘n pop” type place, with owner Maria manning the bar every night, chatting it up with the regulars and getting to know the first-timers, always with a big smile on her face. And while the atmosphere was certainly welcoming to a couple of newbies like us, it was clear there was a large roster of regulars. Photo collages decorate the walls, covered with drunk happy people I presume to be Whirlaway enthusiasts. In fact, one of the guys sitting at the bar told me that he was in a few of the pictures, taken years ago. A super friendly place, if you ask me.

Wondering where the name came from? The rumor goes that the original owner put bet on a horse that wasn’t favored to win, but eventually became the triple crown winner. With a good-sized hunk of change as his winnings, he opened the bar and named it after the winning horse: Whirlaway.

Upon leaving I felt the urge to say “thank you” to Maria, as if she were our host for the evening (or at least the last hour of it). I’ll definitely be back to hang out on the well-loved couch and play a game of Jenga, while picking out tunes from the great jukebox selection. The Whirlaway is a keeper.


And there you have it: UPchicago bar crawl numero dos, finished. And what a fun one it was. We pride ourselves on knowing a decent amount about this great city of ours, but I won’t lie when I say I haven’t spent an inordinate amount of time in Logan Square before. This night changed all of that though — for a few of us, I think. We’ll be back, hanging around the Whistler and Cole’s on a weeknight sipping a beer, or a 100 proof bourbon in Phil’s case… so keep an eye out for us.

Oh, and special shoutout to Phil, who not only conquered his fear of bourbon that night, but provided the group with sustenance along the way. Andes Mints and gummy worms make for great in-between bar crawling treats. Well played, my friend.

Now get out there and try this one with your friends! And let us know what a frickin’ awesome time you have.

Map it:

Logan Square Bar Crawl

*Link Photo Credit: Flickr: swanksalot

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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