1. No one hangs out in the Loop
Chicago's city center isn't a hopping place like a lot of other major American cities. If anyone actually lives in the Loop, I have no idea where they are. Most of the restaurants, bars and shops close before midnight, and there aren't many gems in the first place.
2. Jeppson's Malört tastes good
Malört gets a bad rap. Sure, a shot of it tastes like a wormwood plant was lit on fire atop your tongue, but shots are a pretty nasty experience in the first place. At least Malört makes throwing back a glass of booze interesting. After you've gotten over the initial disgust the drink usually induces, you'll probably learn to like it.
3. Not everyone is a Cubs fan
Chicago's North Side baseball team is notorious for its 107-year championship drought, but there is an entire other baseball team in Bridgeport. Also, the White Sox won a World Series title in 2005, making them the most successful Chicago sports team outside of the Blackhawks this century.
4. Rahm is incredibly unpopular
After being appointed President Obama's chief of staff and being elected to two terms as mayor of Chicago, it's easy for outsiders to think that Rahm Emanuel is a likable fellow. But after sweeping CPS school closures and reforms that haven't exactly benefitted Chicago's lower-income neighborhoods, he's less popular than ketchup on a hot dog.
5. Don't go to a steakhouse for dinner
Yes, Chicago Cut and Kinzie Chophouse are ritzy downtown restaurants, but you can get a good steak all over the place. Get out of River North and dip your toe into the city's awesome, weird and eccentric culinary scene.
6. Walk up the escalators, or stand on the right side
Tourists posting up on the escalator with their massive bags shouldn't be surprised when they get shoved out of the way by a busy Chicagoan who's late for work. It's shaped like stairs for a reason, people.
7. Yes, our cigarettes are that expensive
Chicago, and the state of Illinois in general, taxes the shit out of tobacco products. On top of that, Cook County just raised its sales tax by an additional percent. If you wanted cheap cigarettes, you should've stocked up back in Iowa.
8. It's cool for cyclists to bend the traffic rules
A cyclist blowing through a stop sign or a red light can be disconcerting to many out-of-towners, but as long as they're not riding around like a maniacal asshole, cops generally look the other way.
9. The grid system is incredibly simple
Most of Chicago burned down in 1871, which made way for one of the best-planned cities in the world. There's no reason why you should ever be lost in Chicago—every "100" on an address is equal to a block away from the grid's origin at Madison and State.
10. The city isn't that dangerous
Chicago's murder rate comes up in national press on a regular basis, but if you look at homicides per capita, we're really not that bad. New Orleans, Kansas City and Oakland all have a worse murder rate than Chicago, so there's no reason why you should worry about getting shot on your next trip to the city.