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A weekender seems like the classy decision—at least until you arrive at PDX at one end of the terminal and have 15 minutes to make your connection on the other side. Better get a run on with the uber-practical Timbuk2 Never Check 4 Wheel Spinner. This rolling bag fits perfectly in the overhead while cinch straps ensure no one’s sticky fingers are getting into your stuff. Front pockets provide quick access to segregated items.

Buy Now $289