I've lived near or around Chicago my whole life, and specifically in the city for four years. At this point I think I get it.
Here's what you need to know about Chicago before you come here.
Learn how to complain.
People in Chicago have two jobs: the first is the one they get paid to do, and the second is part-time complaining about the weather. Rainy. Windy. Cold. Hot. Nothing satisfies the people of Chicago and they are always baffled by anyone who moves here from a warmer climate. Of course if anyone from that warmer climate DARES TO INSULT THE GREAT CITY OF CHICAGO we know how to passive-aggressively tell you that we just love the change of seasons and we don't think we could ever live without it.
Chicago is not the end of the world, weather-wise.
I drove from Chicago to Wisconsin in January and I will tell you, Chicago doesn't even know the MEANING of the word snow. "Oh but what about that snow storm we had that one--" --PUNY NONSENSE SNOW, I will interrupt, COMPARED TO WISCONSIN. Wisconsin eats snow for breakfast. And I imagine so do many other northern states and that place above Wisconsin, Ol' What's-Its-Name. Yeah, it gets windy and snowy and horrible here and it makes you want to curl up inside a Tauntaun. But at least we have salt for the roads and trucks to distribute it. Do you know what Wisconsin uses to keep their billions of feet of snow off the roads? SAND. But like, a child's sandbox amount of sand. What are you, Houston? Wisconsin, you care just a LITTLE too much about those lakes of yours. If your fish refuse to adapt to the salt, just buy something more tropical. I'm sure they'll adapt.
The secret to surviving winter
Two things: Preparation and not bothering to care what you look like. A coat from an authentic sporting goods store. Multiple gloves at once. A hat that is so big and fuzzy that it is possible it's still alive. Large, weather-proof winter boots that can trudge through dark grey slush. Basically, the closer you are to looking like an Inuit, the better. They know what they're doing. If you can wrap yourself up in an actual polar bear, you have done your job.
It always snows once in April.
I am telling you right now: there will be a day in March. Maybe even a few days. On that day, it will seem magical. It may even be 60 degrees outside, dare I say 70. Every year this happens. And every year on that day I tell people "It always snows once in April." And they laugh. Oh! How they laugh. "You fool!" they say. "Weather cannot change!" They put on shorts and flip flops and wonder why no restaurant has put out its outdoor cafe seating. But the restaurants have learned. And so have I. I have held this "April" theory since college. Chicago has never let me down. Every year it comes back. Usually not too harshly. But it snows. Oh! How it snows. And all the idiots who vow that they'll never go back to pants have to walk around, their teeth chattering, pretending they never heard my warning. But they heard. They heard.
The summer is freaking awesome.
Because of our deathly winters, Chicago comes alive in the summer. There are literally festivals on every weekend. Free concerts, movies in the park...all kinds of things. Check out metromix.com to find fun stuff.
We're on a grid.
After the Chicago fire, this city had a chance to rebuild itself smartly. One thing they did was put everything on a grid system, where almost every street goes either north-south or east-west. That makes it easy to get around. However...
Some roads go diagonally into the city.
These roads are generally annoying because they mess with intersections. The worst of them being Elston Ave...Ohhhhhh Elston, how I loathe thee. But I'm getting ahead of myself. Stick with the grid and you'll be fine.
Some Chicagoans understand location based on the address numbers.
They say things like "Oh, 1400? that's really far north" or some nonsense. These people are freaks. Most of us just give main cross streets. "Broadway and Foster" "Damen and North." Eventually you'll learn these roads too and these intersections will mean something to you as well.
A proper Chicago hotdog
If you don't know, the Chicago dog is piled with everything besides ketchup. I don't know why we are so opposed to ketchup on our sausages but it is just our way. Most places won't blink if you order ketchup, but I suggest you try the true Chicago way just once. There are plenty of places for them. Check Yelp, or go to Portillo's.
A proper Chicago slice
Chicago pizza is usually served deep dish. It is intense. One to two slices will suffice, and you have to eat it with a knife and fork because it weighs about 80 pounds. Giordano's is well-liked and there are tons of them around, although I'm partial to Lou Malnati's. Lou's isn't for everyone--the sauce is chunkier and less sweet, and the crust is buttery and crunchy, not bready. But it should be tried. Stay away from Uno's. It's not worth it.
Thin crust pizza in Chicago often comes cut into squares, not large triangles like New York. It's good that way; you have no idea how many you've had and can pretend like it wasn't much.
In order of expense: Whole Foods, Dominick's, Jewel, Trader Joe's, Aldi. I'd personally stay away from both end caps. But that's the Middle Class Girl talking.
We have them. To say Chicagoans only "like" food would be doing us a great injustice. I mean, sure, our winters aren't as bad as some, but they're enough to keep you indoors for 9 months. We've got good restaurants, and all the kinds you want. We also have been home to immigrants from all eras, which means delicious foods from around the world: Polish, Ethiopian, Irish (Fadó is Irishman certified), Turkish, Mexican, Detroitian...we have it all, and it's all good. There are tons of independently owned restaurants if you get away from the city, like in Wicker Park (Division and Damen) and in northern Andersonville (Clark and Foster). Again, Yelp that shizz.
Where to start:
If you're looking for a good place to move to in Chicago and you don't know the area at all, I suggest you check out Lakeview. Unless you consider yourself a little more Indie/Hipster, then I say Wicker Park. Both these places are pretty generally well-liked. They have a lot to offer, lots of shops and restaurants and they're close to public transportation. From there you can do research into the other neighborhoods, but here's a small list to get you started:
This is insanely stereotyped and obviously not the final word, but here's who tends to live in some of the neighborhoods you'll hear about, in no particular order:
Streeterville: Newbies, Rich people
Gold Coast/River North: Old Rich people
Old Town: Young rich people
Lincoln Park: Newly college grads
Wrigleyville: Frat guys
Boystown: Young gays
Pilsen: Hipsters, Mexican-Americans
Wicker Park: Rich hipsters, Mexican-Americans
Bucktown: Richer hipsters
Logan Square: Poor hipsters, Mexican-Americans
Ukranian Village: Reformed hipsters
Chinatown: Chinese-Americans (surprise!)
Uptown: Crazy people and corporate gays
Andersonville: Lesbians, Sweeds
Edgewater: A melting pot of immigrants
Rogers Park: Rich college kids
Roscoe Village: Dinks
Lincoln Square: Saxons
South Loop: Couples with dogs
West Loop: Greek-Americans
Humboldt park: Puerto Rican-Americans
Hyde Park: Obama
(Most of these are north side, because I don't know much about the south side. You'll have to sleuth on your own if you want to move there.)(Also, there are SOOO many more than these but I ran out of brain power.)
I've lived in 4 different neighborhoods and I still haven't made up my mind about my favorite neighborhood. They're all pretty great in their own ways.
The neighborhoods are still very segregated.
If you couldn't already tell based on how I just described the above. But I'll let the numbers speak for themselves. Check out this map.
5. PUBLIC TRANSPORTATION
All the information about the CTA is here. But let me break it down.
There are three kinds of cards.
1. Unlimited paper cards. You can buy these at grocery stores and you can ride as much as you want for 1, 3, 7, and 30 days.
2. Pay-per-ride cards. You can buy these at the el station with cash. Each ride is $2.25 per ride, no matter where you go. Put as much or as little as you want on these cards.
3. Magic plastic CTA card that automatically refills with money. You can get that online.
The el, which we also call "the subway" or just "the train" (or at least I do because I'm too lazy to remember words), runs like a spiderweb into the city and back out again. A lot of it does run above ground, but the red and blue line run underground once they get to the city. These two are the fastest lines and the only two that run 24/7. These are the only two lines I've lived along, so I know them the best.
All the el lines transfer to the other lines at some point or another, although it's not always the fastest way to get around. Often the best route is to transfer to a bus. I always check Google Maps for the fastest transit directions. Gmaps is your friend. Use gmaps.
I hear people say that they're too scared to ride the buses all the time, but they're harmless. They basically just run up and down one street. If it runs up and down Grand, that bus is called "Grand." It's really hard. Again, Google Maps will help you figure that part out anyway. As for paying, if you already have a card, there's a place by the driver where you use it just like on the el. If you only have cash, you can put that in the little machine and it sucks it up. But there's no cash back so pray you have quarters.
I've never had a car in the city, but I'll tell you what I know.
Parking downtown is insane. Avoid! Avoid!
It's near impossible to find street parking, and the parking garages cost more than a Donald Trump haircut. If your destination is downtown, a taxi or the CTA is your best bet.
Street parking elsewhere in Chicago:
Some places you pay. We recently replaced coin meters with ones that'll take credit cards, which is clutch.
Some side streets are free, although these ones are usually pretty full, of course. Some side streets require a permit.
No matter what, you're going to need to learn parallel parking. It's the only parking you'll do for a while.
Parking where you live?
Your apartment may have a spot that you'll probably have to pay for, although some places give it to you for free. That one's a toss-up. Just like whether or not they make you pay a move-in fee (BAH, don't get me started), it depends on your landlord. If you're living in a walk-up (an apartment with 3-4 apartments stacked on one another) you're more likely to get cheap parking. The high rises will cost you. If you can live without a car, I say go for it. I've survived so far on borrowing others' cars, renting cars, and taking public transit. Although I have a few friends who have used zipcar.com, too.
In the winter it's hard to get a spot because the street cleaners are not particularly precise and snow covers a quarter of the spots. Once you finally dig yourself out/into a spot, some people find that spot hard to let go of it. So they put old lawn chairs out to save their spot. It's pretty much crap and a point of contention for Chicagoans every winter. In the end, it persists because people are afraid if they move the lawn chairs, they'll be keyed.
This is a big city, so of course there are tons of places to see regular concerts and plays and stuff. Here are a few slightly more underground:
Second City: Improv
Steppenwolf: Weird theater
The Neo-Futurists: Weirder, smaller theater
The Vic: Smaller concerts and stand up
Music Box Theater: Film festival type movies
Landmark Cinema: Film Festival type movies...but the ones with Sean Penn in them
Buddy Guy's Legends: Authentic Chicago blues that will ease your soul.
You know all those jokes New York people make about homeless people pooping in boxes? Yeah, we have those people, too. I've seen some crazies. I've HEARD some crazies. I've been approached by crazies. But I have never been hurt by a crazy. They smell like the pachyderm house at the zoo, they ask for any food you can spare and then get mad when you give them your sandwich because they wanted Wendy's (*true story*) they sing loudly. Everyone has a few stories about crazy/drunk people on the el. My personal favorites:
1. The guy who announced everything the P.A. voice did, with the exact same timing and intonation.
2. The guy who kept yelling "MATA LA GENTE" which I confirmed via phone meant "kill the people." That one was by far the scariest. But he got off the el without touching a soul.
There are stories. People being beaten or jumped. And apparently lately there have been these mob attacks where a bunch of kids jump on a bus, take everyone's stuff, and jump off. And the morning news is not exactly the best time to look for feel-good stories. Almost every day, a child on the South Side has been killed and someone was found in the lake. Safety is not to be taken lightly, for sure.
All I can tell you is, I've never had anything stolen from me (KNOCKS ON ALL THE WOOD) and I've never been hurt (AGAIN WITH THE KNOCKING). Keep your headphones in your pocket at night, and stay alert. But we're still Midwesterners, and most of us still have the decency to keep our hands to ourselves. We're also a city, so the streets are well-lit and well-populated. Use those to your advantage.
9. YOUR APARTMENT
Nine times out of ten, your apartment will look like this:
It will be a walk-up, huge, with tiny bedrooms off to the side. It is the Chicago way. A landlord told me that this was because, before central heating, people did nothing but sleep in bedrooms because they were so cold, so they didn't bother making them very big. So if you go looking at apartments, expect this general look.
If you've never lived in cold weather:
Go to a hardware store before winter sets in and buy this stuff to go over your windows. Especially if you have old windows, this will cut down drastically on your bill and cut out drafts.
Yikes. I am the last person to tell you about sports in this city. But it's important for you to know the basics if you want to live here. We are REALLY into sports in Chicago. So for those in the dark, here is the breakdown. If you want deeper info than this...you're in the wrong place.
The Bulls. Red, Black and White. We used to have Michael Jordan and once he left, we were only okay until this year.
The Bears. Navy and Orange. We used to have Ditka and once he left, we were only okay until we got Urlacher, a white dude with an insanely large neck.
Cubs: North side. Blue and red. The stereotypical fan is white, rich, and a prat. We are infamous for having a 100 year losing streak, and famous for Harry Carey and an analog scoreboard.
White Sox: South side. Black and white. The stereotypical fan is...well, the opposite of a Cubs Fan. The Sox won the World Series in like...2005?
Blackhawks: Red and black. This is the jersey they wear in Wayne's World. Everyone forgot about hockey around here until last year when we won the Stanley Cup and suddenly everyone became enormous hockey fans. I found it annoying, but I guess good for general morale.
Chicago Fire: Navy and red. One time, two players from the Fire came to our junior high and played Keep The Ball In The Air with one of my classmates, Paul. Paul won.
Okay! That's what I have to say about Chicago. Hope this helps any newbies (or potential newbies who are thinking about making your way here). Any other Chicagoans make it all the way through this thing and have anything to add? Comments welcome and requested!