25 things every Chicagoan should know how to do

You start to learn things about Chicago after living here a while. RedEye staff members feel we'd be ignoring our civic duty by not clueing you in on some of the best tips and tricks we've acquired over our collective years. Call them ... Chicago hacks? Never get gouged for baseball tickets: I have employed this strategy for both Cubs and Sox games for years. Note that it almost never works during big rivalry games or the Crosstown Classic and you have a better chance of success during mid-week games.

  1. Wait for the game to start. Seriously. Post up at a bar or the tailgate. Walk up to one of the brokers (not the scalpers, mind you. There’s a difference.)
  2. Low-ball the crap out of them.
  3. Watch you some baseball.

Work the damn grid:
There’s no reason you shouldn’t be able to navigate around the city. We should be lucky we even have a grid system. Have you been to Atlanta? It’s like someone got drunk off peach brandy, opened up “Sim City” and just went for it.

 Here’s how it works:

  • The beginning of the grid is at Madison and State St. Which is why they’re listed as 0 E/W and 0 N/S.
  • All the E/W streets in the city are coordinated by how far they are from State Street. Ditto N/S streets from Madison.
  • 800 units (that’s city blocks for the slow kids) on the grid system equals one mile.  
  • So, let’s say you’re having a few beers at Quenchers at the corner of Western and Fullerton. (Do this. They have good beer.) Fullerton is 2400 North and Western is 2400 West. You are 24 blocks both ways from Madison and State and the “center” of the city. (Why they chose to divide the numbers by 100 is beyond me.)

How to actually get into Girl & the Goat:
If you don’t have reservations, the best time to go to Stephanie Izard’s popular West Loop restaurant is right when it open sat 4:30 p.m. (There will be other die-hards lining up, so plan accordingly). You’ll have the choice of beelining for a barstool or, sometimes, nabbing a seat at the chef’s table near the kitchen if it isn’t booked until 6 p.m. or later.

Stay outta the cold. So you’re downtown shopping, meeting a friend or going to the dentist, and the weather sucks. No worries—the Pedway can make your walk much more pleasant. Lots of parking garages are connected to it, too.

Get drunk at Lollapalooza for less: Buy the wine. They give you a frigging bottle’s worth over ice (We call it “The Stepmom”) in a big commemorative cup for the price of 3 beers.

Navigate Lower Wacker: The upper level is for tourists and trolleys. If you really want to get across town fast, head underground. Hey, it was good enough for Batman!
Avoid CTA frustration when going to a baseball game. Even when the Red Line isn’t under construction, taking the CTA to ball games doesn’t have to be a sweat-fest. Sox fans: Take the Green Line to 35th; it’s a two-block walk to the Cell. Cubs fans: Take the Brown Line to Belmont, and it’s just four blocks to Wrigley. And there are bars everywhere.

Deal with snow: Whether it be shoveling (lift with your knees), driving in (not like an idiot, please) or slogging through the snow, you have to be able to deal with it to survive our winters--usually.

Walk with purpose: I was originally going to put “Use the sidewalk like you have common sense” but this works, too. Walk like you have somewhere to be, even if you don’t. Leave that meandering nonsense to the tourists. This goes double if you’re on a bridge.

Walk with your significant other: It's cute that you're walking around with your sweetie, but seriously, there are other people on the sidewalk. Let go if you're about to face a crowd, or if you need to go single-file. It won't kill you. It won't even break you up, probably.

Keep the heat on: It’s simple. If you’re the one standing by the heat lamp on the train platform, your job is to press the button on the heat lamp.

BYO to Gilt Bar and Bavette’s Bar & Boeuf. Since dinner at one of Brendan Sodikoff’s River North hotspots isn’t going to be cheap, do like the pros do and bring your own bottle. There’s only one rule: You’ll have to offer a glass of what you brought with another table in the dining room, so leave the two-buck Chuck at home.

Find a good apartment: Brokers are good, Padmapper/Craigslist is better, but true Chicagoans know you have to walk through the neighborhood you want to live in to find the best places. (They’re usually owned by some old guy that hasn’t learned how to use the Internet yet.)

Ride the Water Taxi: Two bucks. Takes you from Michigan Ave. at Tribune Tower to Ogilvie Transportation Center. Gorgeous view, cheap price.

Embrace alternative grocery shopping: From farmers markets to produce trucks to bodegas, a real Chicagoan should know where to get good groceries without ever setting foot into a chain store. (Saves you money, too.)

How to eat ethnic: Chicago is a city of neighborhoods. Be able to know where to get a Mother-in-Law, golabki, a gyro cheeseburger and a quality doro wat and not pay a bajillion dollars doing it. Actually, while we’re talking about it ...

How to drink like a Chicagoan. Rules are simple: Handle your booze, handle your bill and handle your business the next day.

Find a secret party: Chicago is like that Whodini song, the freaks only come out at night. Now, social media has made it easier trying to find the secret 7 a.m. rager, but you’ve got to put some work in. Making friends with local DJs and folks in the restaurant/nightlife industry would be my advice. If anything, they’re usually the most interesting people at whatever function you attend anyways.

Get (bleep) done in your neighborhood: Got an issue? Find out what ward you live in (Hurry! They might have just changed again.) Know who your alderman is. Get all up in his/her grill. Repeat as needed until problems get solved.

Own your neighborhood summer fest: There’s a fest on your street! Fantastic, because that means the liquor stores on the corner will almost always jack up the price of canned beer. Buy the night/week before so you don’t get gouged.
Drink at The Billy Goat right: Look, the Goat is a wonderful thing, but rules are rules, and if you ask for fries, you’re going to look like an idiot. Chicago regulars do know that at the Goat, if you know your bartender and tip well, every shot in the house is $5, and you’ll likely get a double. 

Make a cocktail that tastes good using Malort: Get you a cocktail shaker: Put the following in it. 1 ounce Malort, 1 ounce gin, two good squeezes of lemon juice, then fill the rest with grapefruit juice and ice. Shake it like you hate it. Drink. You’re welcome.How to avoid car frustration: If you've got a car and hail from the 'burbs, keep it registered there. If you're also lucky enough to have a garage spot, there's absolutely zero reason to buy a city sticker.How to get high the right way: Don't ever, ever, ever take your out of town friends to the Sears Tower. Every true Chicagoan knows if you've got to take them to something touristy, you suck it up, pop for a $14 martini at The Signature Lounge and enjoy the much better view from the top of the Hancock.

Use your network: Chicago works better when you have connections. At this point, you should be able to comb through your list of friends and find out who’s got the hookup on tickets and other cool things. Remember though, don’t be a mooch. Give as well as you get.

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