The Best Rolling Luggage
Crew 8 Checkpoint-Friendly Brief and 20-inch Rollaboard
This brand costarred with George Clooney in the film Up in the Air and is a favorite among flight crews. A laptop sleeve lets you go through security without taking out your computer, and a strap sturdily holds the smaller bag (shown) on top of the larger (not pictured). Both are carry-ons (the smaller bag fits under a seat).
To buy: $130 each, travelpro.com for stores.