Coats: You'll buy no less than 3 coats in graduating levels of ugliness until you buy the coat that will get you a through a Chicago winter. Your first coat is cute as hell, wool blend, looked gorgeous on Blake Lively in that movie and completely useless; coat #2 will be a mid length fur collared affair seemingly stuffed with a pillow that came off your grandma's couch and about as warm; coat #3 is a full length, down filled, comforter like off a very strange bed. It will be black. It will also be the coat you wear for the next 5 years. It will take you 3 years to get to realize warmth trumps fashion whilst waiting for the El in -40 degree weather.
2. Boots: You will start off with Uggs or something similar because that what everyone on your floor wore. You will get through autumn and half of your first winter; all of it if it doesn't snow. Doesn't snow? HAHAHAHAHa. Sometimes it rains right after a big snow, that snow turns to icy sludge that you will have to walk through to get to your train, bus, job, apartment, favorite bar. Do yourself a favor, buy something not terrible, waterproof, insulated, and named after a rapper.
3. CTA: the Can't Travel Anywhere. The bus schedule is a giant lie. They run at will and in packs like wild dogs. Good luck getting your Ventra to work. The El is a much better way to go. The red and blue are pretty regular; the brown is slow as Christmas and all the other shut down at 9:30 apparently. You must live by a train stop to be considered dateable. Schedule yourself at least one hour to go anywhere, I don't care what fairy tail Google maps is spinning you.
4. Street Festivals: From May to October each neighborhood will shut off a few blocks of a major street to hold a fest dedicated to drinking, music, art, bbq, blues, burgers, oysters, or whatever the f*ck we can get Shock Top to sponsor. They vary from one to three day events, once you've been to one, the only reason to go back is because its on your block anyway. Notable exceptions are Market Days and MidSommerfest; they gays put these on so get your ass down there and shake it.
5. Friends with a Boat: This is the only major US city on a fresh water sea! This will, if you are supremely lucky, take up all your summer weekends. A day out on a sailboat with the city scape over your shoulder, the Air and Water Show, trips up the river to see up close and personal the unique and significant architecture and of course the fireworks by Navy Pier on Wednesday nights. Who doesn't want to be out in the Play Pen, or off of Hollywood beach with the hot boys swimming from boat to boat?
6. Restaurants: Chicago has the #1 undisputed food scene in America (suck it NYC). Where are you gonna eat? Randolph Street? Fullerton Market? West Loop? River North? Logan Square? Pilsen? Bring your paycheck, an iPhone to play on for the three hour wait and your super ability to put up with slow and snarky waitrons who live in nicer apartments than you.
7. Bars: You are in luck, Chicago is the drinkenist town I've ever had the good fortune to live in. Hipster bars, corner bars, dive bars, sports bars, Polish bars, neighborhood bars, gay bars, craft beer bars, Irish bars, Mexican dance bars, karaoke bars, package stores that are also bars and my favorite:Old Man Bars. Most don't serve food so plan accordingly
8. Sports ball: Hawks, Cubs, Sox, Bulls, Bears, Fire, Sky, Red Stars, if you aren't into sports ball, get acquainted, become conversant. This will come to be a large part of your new life. The Cubs are, as I write this, not when you read it silly, in the clenches of breaking a 106 year old curse. If you don't know how hot Chris Bryant is and don't want to have his babies, no matter your gender or sexual orientation, you must immediately pack your bags and move back to Nebraska. Good luck on the farm.
9. Car ownership: Good luck, between the city taxes, licenses, permit parking, downtown parking, the parking tickets as a line item on your family budget and the ninja parking meter readers as well as insurance, maintenance and gas. 4 months a year you will get to shovel your sweet little Mini out of several different parking spots in front of your place until you give up and claim dibs.
10. Bikes! Do you Divvy? There are 5000 Divvy bikes in Chicago alone. Don't be the idiot who rides a bike on LSD. (Lake Shore Drive dingus!) The super awesome bike your grandma bought you for graduation will be vandalized, at the very least. You will have a huge chance of getting doored at least once, you will run as many red lights as is safe, you will use the Lake Front Trail, you will bike downtown, and you will bike trails that take you on a forest trail ride from Chicago to Wisconsin.
11. Dating Outside of your neighborhood: You will meet some hot man or woman at a Subterranean show, the beach, a rooftop party, on a friends boat. You will have cocktails at Lost Lake, dinner at Longman & Eagle, see movies at Logan Theater. It will be a blissful two weeks entertaining your new love in Logan Square. It dies the night you find out he lives in Uptown AND it's 6 blocks from the train.
12.Dating Suburbanites: NO.