How to: Visit Chicago Like a Chicagoan

Some friends posted this on FaceBook recently. It's long and contains a lot of profanity (which I have edited out) Some of the stuff is factual but a lot is just BS.

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? .

Stay at the Tremont. It’s $90 a night, two blocks from the Drake, and nobody worth a dime gives a xxxx 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 dipxxxxs a cool million to design a glass xxxxx 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 xxxxxxx uneducated hick.

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 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 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 yuppies 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.

That should eat up your weekend.

OK, but what I was thinking of doing…

1) Shopping on the Mag Mile. Ahahhahahahahahahah you xxxxxxx xxxxxxx. You don’t have an outlet store in your state? Believe me, I want your money flowing through the coffers of the city of Chicago as much as anyone.
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.
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 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.

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.

Chicago-Style Pizza

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, ) 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:

Hello, I am a two-flat.

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.

This is a picture of failure.

Chicago Meat

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 xxxxx to me just tell me to go to a chain? First off, it’s no chain you ever heard. 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.

Despite never being there, I know this is a reputable establishment.

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
a. Chicago
b. Windy City
c. Beef
d. Dog
e. Gyros
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 xxxx 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 xxxxs off
• becoming a fan of Rod Blagojevich
• bitching about Oprah
• growing a mustache

My reply!

Right off I want to say that Chicago is one of the greatest places to live or visit.

This guy knows a little and doesn't know much. If possible get someone who lives there to show you around. Or, stop at the Cultural Center, downtown and gather up information on places and things that interest you. There's bound to be something that rings your bell. See the neighborhoods (this is best done with someone from that neighborhood)  Do as many of the museums as possible/. Here again pick the ones that interest you most. They're all different. Do Michigan Avenue. It's one of the most beautiful streets in the world. Go from the Art Institute north to the Drake Hotel (Oak Street) Drive on Lakeshore Drive (I prefer going North) Stop in Lincoln Park and visit the zoo. One of the oldest zoos in America. And! It's free. If you dig steak, Chicago's the place to sink your teeth in some of the finest anywhere. There are great steak houses with no chains attached. The Chup House, Gene and Gorgettis, Mortons and on and on (again a local can point out their favorite) For pizza (Chicago style) you can't miss by hitting one of the "Big Three" Uno's (and its sister a block away, Due) Gino's East and Lou Malnati's. It's hard to go a block in any neighborhood without running into a pizza joint. And, usually, they're all good. Once again check with someone from that neighborhood. Italian beef sandwiches are a true Chicago favorite. Portillo's is really good as is Bueno's but for the absolute beef experience go to Al's or Mr. Beef. Anywhere with a sign saying Scala's beef is bound to be right up there with the best. If ethnic food's your thing, hit the ethnic areas. Chinatown, Greek town, Little Italy, Anderson villa (Scandinavian) and many more. Anything you think you want to try is available. Just ask! There a taste-town for every taste. Just a short note on entertainment. It's there! There are possibly more live theatrical productions in Chicago than anywhere in the US. I could go on and on but this is already way too long. If there are any questions I can answer or suggestions I can give you, give a yell!