#1. Do not say that you're a tourist, especially from Chicago.
My friend was asked, "Do you live by Chief Keef?"
#2. Do not ask for directions from anyone.
From experience, most people don't care if you're lost and will not stop to help you. I once got so lost in Brooklyn that Google Maps couldn’t even help me.
#3. Do not make fun of how they say coffee. It’s rude.
While Chicagoans love to extend their a’s and say, “caa-fee”, New Yorkers pronounce it "cauw-fee"/"cough-ee". When you hear this, try not to smirk.
#4. Do not expect their pizza to taste better than ours.
We know the sauce to cheese ratio... New York pizza is actually pretty good, but... some places over power the sauce and lack on the cheese. I will always be biased to deep dish pizza.
#5. Do not expect that the MTA is as easy as the CTA.
The MTA is really not THAT hard to figure out, but it doesn't make sense the first couple days. NYC doesn't have a Clark and Lake like we do (where majority of the line meet). In NYC, you take a train, transfer to another train, and then transfer to ANOTHER train, and then go down multiple flights of stairs to the pits of hell (really, it's hot down there), just to get on the one you need. Download Google Maps, or you just need to know where you're going and PAY ATTENTION.
#6. Do not just put money on the metro card and go.
If you're there for a week, buy the week pass, it's $32 and well worth it. There is also no such thing as a transit tracker there, so you have to just pray that the train is coming soon. Maybe even bring a crossword puzzle book, because you'll be waiting a lot. "New Yorkers don't have time to wait". …Right.
#7. Do not expect that everything is close together like it is in Chicago.
It's not close. At all. There's five different boroughs with a lot of transferring trains, getting on busses and lots, and lots of walking.
#8. Do not expect to spend as much as you normally would.
New York is expensive. For a large black iced coffee, it's $3.15 (with tax as of 08/2015)… whereas, in Chicago it's $2.81 (as of 08/2015). To save yourself money, definitely download and use the Yelp app. But money is for the living only, so spend it on whatever.
#9. Do not think you should just bring dress shoes.
You need shoes that you can walk for miles in, because chances are not being from NYC, you'll get lost, and do a lot of walking just to get where you need to go. It happens to the best of us, how you handle getting lost is entirely up to you. I’ve found that 9 times out of 10, my Chicago ignorance won’t let me ask for help.
#10. Do not expect you can just charge your phone anywhere.
Do yourself a favor and bring a portable charger, because even in some coffee shops, outlets are limited.
#11. There is garbage in front of the building/don’t expect to take shortcuts down an alley.
There aren't alleys in New York, they aren't as lucky as us, they can’t take shortcuts down alleys. Maybe that’s why New Yorkers are always in a rush, there aren’t as many shortcuts from Destination A to Destination B. After being in New York, I learned to love a good 'ol alley and appreciate the garbage men and women more than I did previously.
#12. Do not think their weather is the same as ours.
NYC summer is NOT Summertime Chi. Did you know New York reaches 90°+ in the summer? I didn't. Chicago almost never gets that hot. I definitely did a lot of sweating while I was there. Pack accordingly, because I definitely didn't.
#13. Do not expect there to be bathrooms in stores and food places because there really almost never is.
No tips for this one, we are all just SOL on this.
#14. Don't underestimate the homeless people there.
Just like in Chicago, the homeless people have some crazy, funny sense of humor. One guy even helped my friend and I out while we were there. We laughed together about a sign that called Donald Trump a pendejo and then helped us with the train. But one man was a little crazy, and a nice older women pretended to be my mom to get him away from me (I thought she was confused when she kept calling me 'mija' and waving me over).
#15. Try to not be freaked out by the large roaches.
Some people will tell you, "it's a New York thing", which doesn't make you feel better. The biggest one I saw was probably one-inch-thick and two inches long, and I definitely did freak out, I actually gagged too. People looked at me and knew that I was an outsider, so definitely don't do what I did.
All in all, though, I had an excellent time in New York and want to one-day move there.