The Best Rolling Luggage
Best for Business Travel
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: Unfortunately, this item is no longer available, but please see ebags.com for similar checkpoint-friendly bags.
Vapor Wheeled Laptop Case
Swanky on the outside, organized on the inside, with a removable laptop sleeve and sections for chargers, cords, and clothes. Had the smoothest telescoping handle of all models tested. Carry-on.
To buy: $425, tumi.com.
Hovercraft 20-inch Wide Body
Not too girlie, not too sporty. It’s shorter and wider than most carry-ons, so it slips into overhead bins wheels-first—smooth and easy. A shallow pocket on top keeps travel papers handy rather than swallowing them. Carry-on.
To buy: $235, eaglecreek.com for stores.
Large and Lightweight
Lift 29-inch Upright
With classic lines in a high-tech polyester that weighs 30 percent less than nylon, it holds a serious load and glides gracefully. Built-in fabric handles distribute weight, making hoisting easier. Also available with 360-degree spinner wheels ($10 more) and in 21 and 24 inches.
To buy: $220, samsonite.com.
London Fog 20-inch Rolling Club Bag
This bag accompanied a Real Simple staff fashionista to Paris (ooh la la), holding three pairs of shoes and six complete outfits. Side flaps allow it to expand (it’s bigger than it looks). Adds style to your airplane sweats. Carry-on.
To buy: $220, macys.com.
Best for Short Trips
Crisp, cute, and perfect for a summer weekend. Easy to rummage through in transit—all three compartments are accessible from the top. The handle hides behind a zipper when you prefer to use the leather straps. Carry-on.
To buy: $200, baggallini.com.
Helium Breeze 3.0 28-inch Rolling Duffel
Incredibly capacious. Long handles, plus grips on nearly every side, make it a snap to grab from the trunk. Unlike some rolling duffels, this one has feet, so it stands upright on its own. Also has a silky lined section for your fancy clothes.
To buy: $160, delsey.com for stores.
BRX Excursion Backpack and Explore 19-inch Upright
The backpack clips onto the front of the upright, so you can check two pieces as one. Hardware for the pull handle is outside, leaving more space inside for your stuff. Lifetime warranty. Also in 22 and 25 inches (upright). Both are carry-ons (the back-pack fits under a seat).
To buy: Backpack, $120; upright, $260: briggs-riley.com.
Heys USA 20-inch xCase
Fun, durable, and cool-looking, it drives well even when you’re running for the plane. Solid “walls” protect the contents and make it impossible to overpack. Easy to spot on a carousel or in a dark attic. In nine colors. Carry-on.
To buy: $100, heysusa.com.