Thus I prefer to avoid the term "dive bar" in conversation. I tend to be contextual; sort of like The Supreme Court on pornography- I can't define what a dive bar is, but I can tell you when we are inside one.
The following is a list, not necessarily of the best dive bars in Chicago, but the most instructional; each of these bars has some attribute that will help you answer the question, "am I in a dive bar?".
Sunny Side Tap (Western and Montrose)
Dive Bar Feature: Opens very early.
No one builds a dive bar in modern America. We build gastropubs that throw their fries in duck fat rather than pig fat and some how, for the effort, nachos become $20. Dive bars are carried over from a different time- a time when people had jobs. Back then America actually built and delivered things, which meant people had to work at all hours, i.e. the nightshift would exit at 6 AM, looking to get a beer. Dive Bars accommodated these workers by opening early.
Of course, now-a-days, everyone works for the same market research firm that requires you to be there at 8 AM so you can attend the first of your 15 daily meetings on the company's 'mobile strategy'. In fact, the modern bar does not even open until 5 PM since --God forbid-- you become the first guy in 20 years to have a beer at lunch and probably type something honest into your power point presentation, like "we sell butter- who gives a fuck if people can see the site on their phone?".
If you doubt any of this, examine the change in beer commercials as proof. In beer commercials from the 1980s, everyone had a job: they clocked into work at the shipyard; sweated; and then, at about the 20 second mark of the commercial, clocked out and got blasted together on Budweiser. Seen today, they look more like an ad for a Jobs Bill than beer When's the last time you saw a traffic cop on TV? Compare that to contemporary beer commercials, where it's all jobless, immature men with 2 day growth beards choosing a Miller Light over their impossibly hot girlfriends:
80s commercial (Who we used to build bars for)
Current commercial (Who we build bars for now)
2. Max's And Friends (Clark and Wilson)
Dive Bar Feature: Untrusting
Max's and Friends checks every bill greater than $1 to see if it's counterfeit. You know you are in a dive, when the bartender doesn't believe any of his customers could honestly be carrying a $5 bill. Moreover, they do not check the bill with those fancy, felt-tip pens that banks and even McDonalds use, to see if the bill is counterfeit. No, the bartender (who, bear in mind, just finished a story about shitting into his neighbor's car) holds the bill in the air and hand inspects it with a flash light.
Max's also has one of the surest signs of a dive: an extremely cheap TV. I've often walked into bars that people call a dive, only to see a huge 64" LCD TV on the wall. That is an immediate sign that you are not in a dive, as the owner of this establishment does not believe that his customers will destroy it. At a true dive bar, the TV is usually protected better than the cash register. My old bar in Akron, Mitch's Lounge, used to have chicken wire in front it. And that's because, when carpenters get drunk, they watch a Cleveland Browns game they way most people watch a Klan rally- spitting and screaming in disgust, while throwing bottles. If the TV looks like something you wouldn't be able to give away for free on Craig's List, you are probably in a dive.
Wriggleyville North (Sheridan and Grace)
Dive Bar Feature: Difficult to explain.
Of all the bars on this list, this bar is the closest to graduating out of the dive category, because it's in a nice area and seems to be getting --however slowly-- fancier. This year they put a small sign on the door --about the size of dinner plate-- that named the bar ("Wriggleyville North"). Before that, it had no name and was impossible to explain to friends as a meeting point- which is a good sign of a dive.
NOTE this (lack of sign) is not, by itself, a signal that you are in a dive, as several faux dives --meant to lure ultra-hip scenesters-- have crept up recently. But Wrigleyville North still walks the walk because they have not touched what is still the surest sign you are in a dive: women hate the bathrooms. Dive bars do not have modern, automated bathrooms; sinks and hand dryers that turn on automatically. No, they usually have a bar of soap and a single towel nailed to the door for everyone to share. Most public beaches have a nicer bathroom and women simply can't take this change- even some men can't. I remember being at Pauly's (18th and Union) and a young businessman was waiving his hands under an old fashioned sink, waiting for it to turn on, like was from the future and never saw sinks with knobs before. Five feet a way, a man was taking a dump in a toilet stall that was missing all doors, asking if we had a sports page he could read. The businessman left after finishing his beer.
4. Ethyl's Party (26th and Wentworth)
Dive Bar Feature: Filled with liars
This is probably my favorite bar in Chicago and, I should say, I have no idea if it's legal. They allow smoking; last time there was a nail gun on the floor; the bathrooms often have a bucket of boiling chemicals; people wrestle in the corners and no one complains. It's under a highway so dirt and oil rains on you as you walk towards it. It's filled with character- it occupies a former funeral home, so there are odd semicircles of great decoration within this dump; obviously, those are where the caskets were presented. But it's best feature is the people and the staff: top-to-bottom liars.
Dive bars have great liars. I'm not talking about the kind of liars you see at normal bars, where some one exaggerates his income or falsely replies "yes, I have all Wilco albums" for reasons even he doesn't understand. No, I'm talking about dyed-in-the-wool liars. People who claim to have done the impossible. Men who claim to have outrun a police helicopter in their convertible, or assassinated for the mob back in the 90s; dorky-looking alcoholics who claim they can hack into the CIA for you or make a person disappear on paper. And everyone can get away with these lies at a dive because no one has smart phones, thus we have to disprove Gary's claim about outrunning a police helicopter with our own half knowledge of physics and engineering:
"I don't know Fred, I think helicopters can go, like 300 Mph"
"Yeah, they can go fast- but they are up there! They gotta cover more ground! Ever seen 'em do the traffic report??- It takes them forever to get from one spot to another", I believe Gary.
Even the staff here are liars- beer is a different price every time you ask; they close when ever they want. It's one of the last truly adventurous places to drink in Chicago (that I have encountered).
NOTE: it has no sign because a semi truck ran into their last one and they don't have the money to replace it so the bar is difficult to find. In fact, I have never been able to locate it sober thus, much like all great destinations (The Fountain of Youth, Atlantis), I have been accused of fabricating this bar and that perhaps it does not exist. But I assure you, it is out there some where; an alcoholic's beautiful mirage, made real, some where south of Chinatown
5. Four Treys (Damen and Henderson)
Dive Bar Feature: carpeting
Four Treys is probably the blandest dive on this list but in some ways it's the most instructional as it has virtually every attribute of a dive. First, I have never been in a bar with carpeting that wasn't a dive. Next to scary bathrooms, carpeting may be the surest sign of a dive. Additionally, the exterior has aluminium siding, which is another big sign of a dive; the interior has a false ceilings (i.e. those white square foam boards that fall on your head randomly); unmarked doors that open to closets; etc.; etc. In short, much like the Chrysler Building showcases all the features of Art Deco architecture, Four Treys sums up dive bar design. The free counter space is covered entirely in local menus because, like all great dives, they have no kitchen and also no understanding of how much easier that process is on a smart phone over physical menus. They talk about their karaoke machine like it's a mainframe that can predict weather; etc., etc. A great bar and, more importantly perhaps, an even greater bar for understanding dives.
Special Guest Contributor: Sean Flannery
Flannery is a prolific comedian, producer and writer with credits too numerous to name. He's the creator and host of The Blackout Diaries a wildly popular a Saturday-night showcase where stand-up comedians, plus ‘"regular" people tell true drinking stories - Also Named Chicago's best drunk by the Chicago Reader