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First Flight: Carry On + "Personal Item"?

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So, I'm going to study abroad at Cambridge for 5 weeks starting in July. I've never flown before, and I'm flying United, so I wanted to make sure that I get the luggage situation right before I show up at the airport and end up having to check everything for a ridiculous amount of money.

From what I've read on the UA site, the first checked bag to Europe is free, so I can pack most of my stuff, clothing, toiletries, etc. in one big roller bag and check it, right?

Then, I'm allowed one carry on bag, max. of 45 inches, or max of 14 x 22 x 9. I have a bag that I'm pretty sure fits these dimensions, but I'm concerned the depth might be slightly over 9" when filled with stuff. However, it's only 20" high and 13.5" wide, so even if the depth measured 10", it would still be less than 45 (43.5 to be exact). As long as it remains under 45", will it pass inspection as being an "okay" carry-on if it's pretty close? Or are they really, really strict about it being exact?

Third, I'm allowed one personal item, but of course, UA doesn't specify dimensions for this item. It does say this can be a laptop bag, which is what I was planning on taking. I've heard that one airline specifies 36 inches or less for the "personal item", and that this is a good rule for most other airlines, too. But I just wanted to make sure.

My bag is standard shoulder-strap laptop bag, measuring about 16 x 11 x 3, or about 30 inches. In other words, it's a standard, thin laptop bag that carries up to a 15" laptop and accessories. I was planning on putting all my electronic equipment in it: my 13" Macbook, my Kindle, my iTouch, and their associated cords/adaptors. Now, I've heard such a bag is okay as long as you can fit under the seat. Will this fit? Or will it get me flagged?

Since I've never flown before, I don't want end up with a hassle when it comes to checking/carrying-on baggage. Do my bags sound okay, or should I scrounge around for some smaller ones?

Also, I was wondering about weight restrictions. Do my bags have individual restrictions, or is there a total weight I can't exceed for all bags (carry on + checked) combined?

Thanks,
Ritequette

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