Best Carryon Bag to take to Cancun, Mexico

For cheap bags, check out TJ Maxx/Ross/Marshall's. I got some kind of rolling carryon there over the summer for about 30 bucks. I've used it several times, it's holding up well, and it holds all kinds of stuff. Dimensions should all be printed on the tags so just make sure you've got Southwest's requirements with you if you go to browse.

http://www.tombihn.com/page/001/PROD/500/TB0906. Greatest bag I have ever used. Used it for a 2 week trip to Italy and it held everything. 2 day trip. Exactly carry-on size. So easy to use. Holds so much. Very durable. Seriously. If you can afford a packing cube or two, those are great. Worth the money (if in your budget, of course).

http://ask.metafilter.com/189204/Pack-my-socks-in-what-What-luggage-to-buy to my question a few months ago that lead me to the bag. Oh, and sorry to be vague above. I use it for short 2-day trips (super light) and for longer trips. I travel a ton for work and it is holding up very well.

Take a look at the Red Oxx http://www.redoxx.com/Airline-Carry-On-Luggage/Sky-Train/91019/100/Product. It's designed to airline carry-on specs and fits in the overhead bins even on the smaller regional jets while still holding a ton of stuff. All the hardware is super heavy duty and I can't imagine it ever wearing out or breaking. I also own the slightly cheaper http://www.redoxx.com/Airline-Carry-On-Luggage/Air-Boss/91018-Air%20Boss/100/Product, but really miss the backpack straps when having to trek all the way across an airport to catch a connecting flight.

If you're on the road a lot, the Red Oxx recommendations above are amazing and worth every penny.

Briggs & Riley makes excellent high quality suitcases http://www.briggs-riley.com/category/productDetail.aspx?id=21-inch-Carry-On-Expandable-Upright_U421X&sec=travel. Their http://www.briggs-riley.com/simple-as-that-lifetime-guarantee/ is no lie, they really service the bags for life.

my wife and i took a pair of these to scotland this summer, and they were brilliant - and now they're on sale... http://www.ebags.com/product/ebags/mother-lode-tls-weekender-convertible/143101?productid=1370035

...oh, and do get a packing cube and try the bundle packing from onebag.com - i packed all of my stuff and at least part of my wive's, mostly because mine packed so much more compactly. I'm a convert.

I have the http://www.ebags.com/product/ebags/mother-lode-tls-mini-21-wheeled-duffel/125538?productid=10150071. I fly on Southwest frequently and it fits into the overhead compartments no problem. I like that it expands. I also like that it comes in colors other than black. When I took a bus one weekend, someone grabbed my black suitcase because it looked like his. It has a hard back so I've felt comfortable checking it. I don't like that it doesn't have a shoulder strap or a separate laptop compartment. Other than that, it's a solidly good bag.