We'll know you're a n00b if you ask "but which way is north??" after we give you directions. We talk in four directions here, and we always know which way we're facing. Get a compass or remember the lake is always east, because the streets are long, and the difference between 3030 N. Halsted and 3030 S. Halsted is about eight miles and two hours of hassle. Once you've got that down, the city is actually pretty easy to navigate.
We have a love/hate relationship with the CTA, but we can't hate too hard on a system that gets us to work every day, even if we're always 15 minutes late. If you're waiting for a train during rush hour and one pulls up with an empty car, it's not your lucky day. Someone took a shit in there and it smells. If an old man or a pregnant woman gets on your bus and you're sitting in one of the handicap seats, get up and stand or be prepared to have six different people yell at you until you do.
No one asked for Ventra, but the new app is actually a godsend. It will tell you when your card balance is getting low and allow you to top it off at the bus stop. Also download the Transit Stop app, which gives you bus/train arrival times so you don't need to leave the warmth of your apartment until you absolutely have to.
This is the cheapest/healthiest of all your transportation options, and it's not a bad bet in the summer, spring, or fall. Chicago's a pretty city and is fun to traverse via foot as long as it's not icy or 900 below. Some caveats: don't text and walk and expect not to die a violent death, because you will. Don't walk at a glacial pace on a crowded sidewalk because this will make everyone in your wake hate you with a passion that consumes their entire being. Don't assume that car is going to stop for you just because you're in the crosswalk. It's not going to stop.
These look really, really lame but are actually utilized on a daily basis by people who aren't tourists. Obviously if you're going to rent one please follow all the rules of the road and don't ride on the sidewalk or on the wrong side of the street unless you want to be hit by a car or shoved off your bike by a sassy old woman.
Get ready to hear an earful from your driver about how dangerous and illegal Uber is, and remember to give him a good tip because his business is legitimately being stolen by Uber drivers. You can catch a cab on the street downtown at all hours, but make sure you have a vague idea of where you're going because you may need to give directions.
It's probably going to be the death of the traditional taxi industry, but Uber's rate in Chicago is insanely low. Like, if a cab ride home would normally cost you $18, taking Uber X instead means you'll be paying $12. If you take Uber Pool, it will probably be somewhere around $8-9. For the same ride. It's really hard to justify taking a cab when Uber is this cheap and convenient.
Lyft is cool, too, but it's a little more expensive and not as fast because there aren't as many drivers. That being said, if there's any kind of surge pricing, taking a cab is almost always going to be the cheaper option. You might think you can do math when you're drunk, but you can't, and that's why you paid $150 for your two-block Uber home on New Year's Eve.