There is only one thing I have unequivocally excelled at in life: heavy drinking. And now, one year into my tenure in Chicago, I look back and admire the truly great places that have rendered me happy and incoherent. You have all been cruel lovers of mine; this one's for you!
Best Cocktail
You've seen it here before. The unparalleled gimlet/margarita at The Matchbox. There is no pleasure like the pleasure of sipping a long series of these. Say what you will about the bar; call it cramped, call it uncomfortable, call it inconvenient; you will COME to this bar for this drink and you will find it hard to leave. Zest that motherfucking lime
What you drink: How many times do I have to say it? The goddamn margarita.
Best Beer Selection
I would like to remind everyone that this is a purely subjective list, that these names are only from personal experience and tastes, and once I find something I like, I rarely deviate. So, in what is assuredly a contentious category, I give my vote to Quenchers Saloon. Located near my place (bonus points!) and hosting plenty of live music, Quenchers isn't just an inviting dark place to put back a few, but houses a selection of over 80-some odd domestic and international beers, including the beloved official beer of this site, Bell's Two Hearted Ale. Good God.
what you drink: The specials are always a good place to start; one of the only places I know with Quilmes readily available.
honorable mention: The Rock Bottom Brewery. I have a serious fondness for micros and any beer that aims only to fuck your shit up. See the seasonal beers and drink yourself retarded.
Best Bar Food
No competition whatsoever, Skylark. A bar that looks nothing at all like it tastes, it's a large innocuous place with a few mangy hipsters hanging around. When I was told I was in for the mac n cheese of my life, naturally I scoffed for I am a macaroni champ. And then I shut up and ate/drank my dinner. Glorious, holy, and unfuckingbelievable. Go there and eat, brethren. Spread the gospel of Skylark.
what you drink/eat: Another honorable purveryor of Bell's Two Hearted. Do yourself a favor and go decadent: Bell's, tater tots that will blow your mind, collard greens as you've never tasted them, topped off with the macaroni n cheese. If you die, it will be in the most complete, sated happiness you've ever experienced.
honorable mention: Not actually a bar, but no less dear to my heart, Won Kow is one of the oldest dim sum establishments in Chinatown. $2 Tsing Tao and some of the finest tasting dumplings. For best results, get there early on Chinese New Year and tie on a serious buzz with friends before hitting the parade.
Best Music
God help me, another category bound to get me lynched in this town. But for sheer awesomeness of acts, atmosphere, crowd quality (see: ratio of hipsters to me), and fucking affordability, I give it to Schuba's. My heart has been broken twice now in the space of a month having missed the likes of Elvis Perkins and Dan (holyshitareyoufuckingkiddingmetheguyfromtheblackkeys?i wouldmakeallhisbabies!whyyyyyyyyyamimissingthisshow?!!?!iwanttodie...) Auerbach. Couple these allstars with the fact that my friend's band has also played there on numerous occasions and drawn a crowd, and you have yourself a refreshingly unpretentious venue. Ignore the fools with their Ginsberg beards and PBRs. You are here to rock. And no one is going to stop you.
what you drink: Keep it simple. Bottled domestics - the waitress will be good to you while you dance your little heart out.
Best Atmosphere
I am a lover of novelty and deviance. You know these things; you're no stranger to my scribblings, Dear Reader. So this category goes to The Old Town Ale House. It's a close, dark dive (as all these bars are) with every inch of available wall space covered in portraits. The paintings are done, I understand, by the owner, and the subject matter ranges from frequent patrons to political figures. I arrived on the doorstep of this bar when word spread (circa the last election) of a scurrilous nude portrait of Sarah Palin. Buyer Beware: human paint-flesh is in no short supply here, and if you're some sort of uptight fascist, you should stay away. But if you too have imagined the ample breasts of Ms. Palin as she grins and clutches a rifle (Freud? Are you listening?), then I suggest making the trip.
what you drink: Standard fare here. You come for the happy crowd and interesting eye candy.
honorable mention: On the complete opposite end of the spectrum, we have Guthries. Going to Guthries is like stepping into someone's living room. The place is warm and lamp-lit. Small tables covered in red-checked tableclothes. More board games than you can handle waiting to be played. Quiet winter evenings were made for a good round of Trivial Pursuit and some fine bourbon, neat.
Best After-Work Dive
Brando's is hidden in a quiet spot in the Loop, beloved of long-gone deranged capitalist alcoholics who would sooner escape into the bottom of a glass than suffer another minute in corporate hell. As I am pretty much the opposite of this (for now), I come to Brando's with the expectation that I will be leared at, but not bought a drink; be the subject of an overloud hateful accusation directed at women (those bitches), but offered protection or an apology should some out-of-line outsider make a move. The place looks to have been remodeled with the hope that the clientele would be escorting high-class hookers. Abundant red velvet and blue lighting. But these hopes must have faded, since there is always some basketball game on tv and lovelorn Springsteen in the air.
what you drink: There are some wicked martinis to be had in these parts, but I stick to the whiskey sour or some kind of assy Budweiser product to remind myself I don't want to be here in 5 years' time.
Best Overall - The Bar All Bars Should Strive to Be
An easy pick for me - Delilah's. I have loved many bars, but none so well as you. Shall I name the reasons? Dark and intimate. A rotation of local artists' works on the walls (last I saw, a collection of unicorns doin it). Amazing punk and rockabilly music all the time at volumes that make your eardrums beg for mercy. A bartender that looks like James Dean. Zombie movies on in the afternoon. Draft beer that will give you a hard-on. A whiskey selection that will make you straight fall on your knees and declare your undying devotion. Oh, and the occasional promotional event in which they hand out free scotch. Free Scotch! I'm no scientist, but I'm pretty sure free scotch cures cancer. And AIDS. And did I mention the many-tattooed James Dean bartender? And I shall name my first born, be he male or female, Delilah.
what you drink: Bell's Two Hearted, when it's available. Piraat, if you're in a beer mood (this shit will kick your ass; i imagine this is what licking a Belgian pirate would taste like); whatever the shot of the month is; absinthe; whiskey/bourbon/scotch.....really, you can do no wrong here.
