[Ed. note: The below piece of writing is extremely funny. It is also extremely profane. The word irreverent does not go far enough. If you’re offended by salty language and off-color humor, please just enjoy our photo today and I promise we’ll be back to our usual family-friendly routine promptly tomorrow.]
[Ed. note part 2: It's also really long. Tough.]
Since moving out of Chicago, I’m asked about every three months for advice about visiting Chicago: what to do, where to stay, what to eat, and so on. I’ve come to realize in these conversations that either (a) I’m a complete slug of a person or (b) everyone assumes I spent twenty-eight years in Chicago living as a tourist. While (a) is probably true, this article is about (b). People will ask me about a restaurant like Charlie Trotter’s or what I think about the Drake Hotel, and I have to remind people that I was living in Chicago on $40k a year. I make more now ($41k!) and I still don’t stay at the Drake when I fly back home. I guess I just know a bunch of obnoxious WASPs, but I don’t think you learn anything about Chicago by trying to hang around Streeterville and Gold Coast for a long weekend. So below I’m going to compile my true honest-to-god suggestions for visiting Chicago.
Where do I fly into?
I don’t care. They’re both about the same distance from where you’re going to stay. Yes, I know where you’re going to stay.
How much is a cab from the airport? Will the cab driver rip me off?
1. If you take a cab from the airport to downtown you’re a coward. Get on the El. Smell public transportation, you baby.
2. Yes, a cab driver will at some point rip you off. You’re a guest in the city, and you should be happy to overpay our cabbies.
OK, so I’m staying at the Drake…
Hahahahahhahahaha and you’re worried about getting ripped off by a cabbie? You bitch.
Stay at the Tremont. It’s $90 a night, two blocks from the Drake, and nobody worth a dime gives a shit that you roomed where some princess or Oprah or whoever stayed. You didn’t get treated like them anyway.
OK, I’m checked in. Now what do I do?
OK, so here are the things I think I would list as cool things to do in Chicago. No particular order:
1) River tour. If it’s warm out, a historical/architecture tour of Chicago is rad for both tourists and locals. Aside from a nice, breezy trip on the not overly smelly river, architectural tours in Chicago actually have significance. This isn’t your chumpsville city where you paid a bunch of dipshits a cool million to design a glass dildo in the center of your three-block downtown. Buildings in Chicago actually mean something to the history of the city, and you’ll learn something about the meat packing industry, health and sanitation, immigrant migration, and other cool stuff that you probably won’t appreciate because you’re a fucking uneducated hick. Fuck you.
2) Art Institute. Chicago museums are in general the types of museums you have to commit a day to, and I think the Art Institute probably does that experience the best. If you can figure out a way to get tickets in advance it will save you twenty minutes in a line. The “doll-houses” are downstairs, and you can skip the African and Asian art (you fucking racists) and go through the Greek/Roman section and hit up the American classics. That will kill two hours at least, more likely three. You’ve seen about 20 percent of the museum. Also please consider reading (if you can actually read) things about the art. Art has meaning kinda!
3) Get someone over the age of fifty to drive you to Pullman Town. I was lucky enough to tag along one weekend when my dad took a friend of his on a tour of the South Side. See, despite what thirty-something yuppie shitheels in Chicago think, the South Side actually wasn’t always just for black people! You should swing through Bridgeport, over to Bronzeville, down to Hyde Park, through Washington Park to Englewood, and then on to Pullman. Ideally this person giving the tour is Jewish, but I don’t have high hopes for you. Pullman is itself an interesting historic landmark, and there’s a nice little museum.
4) Cubs game. As a Sox fan, it makes me barf to say this, but you’ll get better photos and it’s more interesting to walk around Clark and Addison even though it’s just a bunch of frat guys. Hell, you’ll probably feel pretty comfortable with that.
That should eat up your weekend.
OK, but what I was thinking of doing…
I KNOW WHAT YOU WERE THINKING OF DOING IT’S ALL STUPID THAT’S WHY I DON’T CARE.
1) Shopping on the Mag Mile. Ahahhahahahahahahah you fucking dipshit. You don’t have an outlet store in your state? Believe me, I want your fucking money flowing through the coffers of the city of Chicago as much as anyone, but if you came to Chicago to shop you are human trash and I hope you die.
2) Going up the Hancock/Sears Tower. Wow, you went up high. You were higher up when you flew in. Also, you’re going to spend too much on a drink in the Signature Room while sitting next to some screaming kid. Great move, asshat.
3) Seeing a show. Yeah, you aren’t going to see anything interesting, you’re going to see some musical prepping for Broadway or back touring. Wait for it to come to your dumbass state, maybe? You could go to iO or a million other great improv troupes or small theaters, but risking being in a theater where you might have to have a thought about what you just saw is likely for you pretty scary.
4) See the Bean without a local. Seeing “The Sky Bridge” seems like such a great idea too, right?! Millennium Park is like a park but without all that history and gravitas that real Chicago parks have. If you don’t have a fat half-Italian bitching about Daley as you try to take your stupid reflection shot, you’re incapable of raising children right. Ponder that.
5) The Taste. I hope someone shoots you.
OK, I am properly humbled. Now, WHERE DO I EAT CHICAGO HAS GREAT FOOD RIGHT GREAT FOOD FOOD FOOD FOOD STUFF FOOD IN MY MOUTH I NEED TO BE A FAT PIGGIE.
OK, now here’s where we get serious.
Eating like a Chicagoan means understanding you can get good to great food anywhere. Yeah, I’m sure Rick Bayless has had his proverbial knob gobbled by every Food Network person you watch, but it turns out if you don’t go to some rib joint that’s open until 1 a.m. you may as well be a plantation owner. So here are some quintessential Chicago dining experiences.
Yeah I know you went to Gino’s East or Giordano’s or whatever. You did it wrong. First off, you ate at the restaurant. Second, you were probably mostly sober. In no way is that how you approach eating a Chicago-style pizza.
1) Go out to a dive bar on the north side (anything west of Southport and north of Belmont will count, I feel; YMMV) and begin drinking. If they have PBR you should have at least two. Same with Schlitz. If you want to do the beer snob thing, you’re welcome to it. Same with scotch. No wine. Vodka is OK.
2) Keep drinking.
3) Begin talking to locals. They will be the interesting people around you.
4) Become best friends with locals. It should be about 10:30 by now.
5) Keep drinking. Decide if you are going to try to sleep with any of these people.
6) At 12:30, begin talking about how you’re hungry. This will be true as you have not eaten.
7) Convince your new friends to take you to their apartment. It will look like this most likely:
8) Order a deep dish from Chicago’s Pizza.
9) Fifty minutes later, make a major ordeal about how you are going to pay this delivery guy.
10) Eat a slice of the pizza that you have somehow paid for.
11) Fall asleep on couch, not having sex with locals.
12) Wake up four hours later. At this point the pizza should be sitting on the coffee table across from you. The cheese has congealed and the sauce gone cold. Think to yourself “There is a block of cheese inside of me. It has to get out…right?” Ponder your life failures as you sneak out of this person’s apartment and try to find a cab/el stop.
Oh you want to go to a steakhouse? Ohhhhhhh hmmmmmm yeah no. Half the places out there are chains, and you aren’t mafia enough to pull off being in the ones that aren’t. Chicago meat to you can be summed up as HogDogGyroItalianBeefSausageBurger. Also ribs.
The shortcut to all your Chicago meat needs is Portillo’s. I know what you’re thinking: did this guy who can’t stop being a prick to me just tell me to go to a chain? First off, it’s no chain you ever heard of so put your dick away. Second, go ask around about Portillo’s and see what kind of reaction you get. Portillo’s is like the only popular thing Chicagoans like that’s not named Derrick Rose.
But, if you want to live it real, avoid Portillo’s and find your own hole in the wall. To do this, first you look for a sign.
Your keys to spotting this place are:
1) Vienna Beef logo on their hanging sign
2) Their name includes one or more of the following
b. Windy City
f. The name of the street you’re on
g. The name of a street you’re not on
h. Any ethnic sounding name followed by an “ ‘s ”
3) Their staff appears to all be related or from the same ethnicity
4) They have any of the following
a. Signed pictures of the old mayor
b. Railroad paraphernalia
c. A picture of a giant hotdog, possibly floating in Lake Michigan
d. A menu hanging above the counter that appears to have ~50 items
e. An elderly lady working the cash register
You should expect to eat here a few times. You will want to try a hot dog (plain), another hot dog (everything), Italian beef (hot peppers), Italian sausage (peppers), gyros (everything, pronounce it “euros” or someone will slap you in a just world).
Chicago Ethnic Food
Chicago is good at ethnicities and racism. It’s a good mix, as it means you end up with very particular neighborhoods and streets (ghettos?) to experience unique foods. Here in Texas, I’m not sure if most people can tell the difference between an African American and a Latino, but in Chicago my old barber (Uncle Joe!) once gave me a lecture on exactly when the neighborhood went to hell: when the Irish moved in.
So while in Chicago, you should at least try to get someplace weird. While I think Andersonville and Rogers Park are two great places to do it, I’m going to send you to Uptown. Uptown works for three reasons. First, it’s accessible, right off the Red Line. Second, it has an energetic corner at Lawrence and Broadway. Third, the Green Mill is there. And fourth, there’s a rad Ethiopian place called Demera. If you’ve never had Ethiopian food before, I expect you to go. Do not google anything. Do not be a coward. Do what they do and stop crying. If you’re lucky, you’ll also get to see a guy perform guitar there and drink some honey wine. Once you’re done, go across the street to the Green Mill. Pay the cover. Listen to whatever weird experimental Swedish jazz band has flown in to play there and just there. Shut your gaping mouth and just try to appreciate what is happening. Please. Try.
THAT’S A LOT TO DIGEST, LOL.
I get it. A pun.
OK, so this should get you through your weekend in Chicago such that I will give a crap about what you did there. Other things to consider may be:
- getting into a fight with a homeless man at an el stop
- having a terrible opinion about sports and sharing it with everyone
- being involved in a gun crime
- eating a plate of fries at Clarke’s and wondering how unsanitary the kitchen is
- going to a Polish buffet on the far northwest side and getting threatened by a three-hundred-pound man in sweatpants
- freezing your fucking balls off
- becoming a fan of Rod Blagojevich
- bitching about Oprah
- growing a moustache