3. The lakefront on a nice day is damn near perfection
Endless fresh water on one side. Stunning architecture on the other. You can go from a skyscraper to a beach in a matter of minutes. Not many cities have this. Treasure it.
4. Don't be a neighborhood hermit
Neighborhood pride is one thing, but I’ve seen far too many Chicagoans become so attached that they barely take the time to explore what else is out there. It’s great that you’ve developed a rapport with the Chinese place around the corner... hey, crazy idea -- maybe check out Chinatown?!
5. Northsiders, ignore the South side at your own peril
A corollary to #4 -- if the only time you travel below Roosevelt is for a Cubs road game at the Cell, you’re missing out, especially in the food department.
6. Make the street cleaning schedule part of the fabric of your very being
Put reminders in your calendar, carry the schedule on your wrist like a quarterback who doesn’t know the playbook yet -- whatever you have to do. The city’s already robbing you blind with parking meters and phantom red light tickets, you don’t need to add $50 to their coffers once a month. Or twice a month. Yes, one time I managed to pick up tickets on both sides of the street on consecutive days. I’m better now. Don’t be like younger me.
7. Make friends with boat people
Boats are really expensive, but generous friends with boats are truly priceless.
8. Your leftover deep dish doesn't go in the microwave
It’s physically impossible not to have leftover deep dish pizza. When you do, show Chicago’s crowning carb-and-cheese-related achievement some damn respect and warm it up in an oven (I think this might be why toaster ovens were invented). When you microwave deep dish it makes Papa Bear Halas cry. Or something.
9. Make friends with your nearest taqueria
Whoever makes the good late-night tacos in your neighborhood is likely going to see you in some questionable states. You want these people on your side. I even had a friend whose preferred joint would extend him a line of credit when he lost his wallet but still needed a burrito.
10. That CTA car/seat is empty for a reason
It’s pee. That's your best case scenario.
11. Guests in town? Hancock over Sears all day.
If you’re playing tour guide and someone wants the obligatory tall building experience, skip the Sears (terrifying transparent overhang notwithstanding) and hit the Signature Room at the Hancock, because if you have to do touristy things, you deserve alcohol.
12. Know when -- and where -- to avoid the particularly soul-crushing traffic
Cubs game days. Bears game days. Air & Water Show days. There’s nothing worse then getting stuck in an unmoving mass of humanity for some big event when you were just trying to go grocery shopping.
This one mostly goes out to those in their early 20s just discovering their freedom. Just because you CAN keep the night going until 4am (5am on Saturdays!) doesn’t mean you should. It also doesn’t mean you shouldn’t, but a discerning drinker knows when to go for it and when you’re just chasing a night that isn’t there.
15. Apartment life is more fun when you're friends with your neighbors
I’ve lived in more apartments in this city than I can count (fine, that’s a lie, I can count them. But still, there have been a bunch!). It’s easy to just stay in your cocoon and give the other people in your building little more than an obligatory entryway head nod when you pass them. Try being a little more friendly -- you could end up meeting some cool people. Or even sleeping with them!
16. Winter's when we need each other most
Chicago winters suck. It doesn’t mean YOU have to, too. Hold the door open for the lady with the kid who’s so bundled up you honestly aren’t sure if it’s a kid or just a really tiny adult. Tip the delivery guy extra for braving the elements because you didn’t want to. And just because you dug your car out doesn’t grant you some kind of lawn furniture-driven property rights. Help your neighbor. We’re all in it together.
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Matt Lynch is a Senior Editor at Thrillist. Offer him a ride on your boat @MLynchChi.