You are going to the US, not the moon. It isn’t a big deal. Take what you need for however long you are going for and don’t sweat it. Any medications should be in their original containers, but I just put everything in one marked ‘Asprin’. No one has ever checked.
I travel all the time and have multiple stamps including work visas from the ME. That always gets at least one question from customs agents. Just answer the questions they ask you. Don’t volunteer stuff. Don’t try and think up witty rejoinders as it seems like you are lying when you hesitate. Be pleasant and smile and above all don’t panic and forget something important, like your name or where you live. Hehe, jinx!
A very important tip when you come back into Calgary and have to go through customs: Avoid the lineups with women customs agents. I have been traveling through that airport for over 5 years now, and I, along with most everyone I travel with agree to this (that’s a couple hundred people, btw). You will spend more time in front of a female agent having her ask you questions, and having a better chance of being pulled aside, than if you go to a male customs agent. I don’t know why this is, and I know it sounds sexist, but from our experience, it seems to be the way it is. I’m all for equality, but I’m more for not having to stand in line and have someone give me the 3rd degree when I’m coming back into my own country.
Make sure you know what the luggage sizes your airline allows for carry-on. They differ by airline.
And if possible, always arrive early to the airport. Yeah, it’s a pain sitting around in the airport, but avoiding the stress of getting there last minute is worth it (especially if you are standing at a security check and can see your plane taking off through the window!). No, this hasn’t happened to me although it has been close. I still shudder at the thought.
Oh, and don’t act like all the other fools in front of you at the security check. You are allowed to start stripping all the change out of your pockets BEFORE you get up to the point where the security guard asks you to. Jesus Christ on a stick, is it to much to ask people to put all their metal items into their bag and take their jacket off before they get up to the scanner? One of the reasons there is a long line is because no one is prepared when they get up there. Does anyone really think that $20 in change, a cell phone, an Ipod, a metal ‘I’m a redneck’ belt buckle, and 5 lbs of jewelry is going to get through the detector without beeping?