Carry on, carry-on

1. Deep pocket
The simple Utility Canvas Overnighter bag has a big inside pocket suitable for an iPod, passport, paperback novels, some extra in-flight snacks and whatever else you’ll need in order to have the best flight ever. The protective rubber bottom means the bag will be durable for many vacations to come. $112 at utilitycanvas.com.

2. Business or pleasure
The Stem Business Bag by Orla Kiely is so cute that once you’ve unpacked, it could easily pass as your everyday bag. The heavy-coated canvas on the outside means it’s waterproof and safe for the beach, too. $195 at Flight 001, 1133 N State St (312-944-1001, flight001.com).

3. Big bag theory
Size restrictions for carry-on bags vary with each airline, but it’s a safe bet that any bag smaller than 22 inches long will fit in most overhead compartments. This big Carry-on Expandable Wheeled Upright by High Sierra Sport Company just makes the cut, and has plenty of pockets and storage space for stowing in-flight entertainment and personal items. $129 at luggagefactory.com.

4. Back it up
Backpacking through Europe doesn’t require a huge bag—and neither does the flight to get there. The midsize Lighthouse Backpack by Land’s End has a padded section for a laptop (so you can blog about your trip at every stop along the way) and plenty of pockets on the inside and out. There’s room for an extra change of clothes, just in case you spill your in-flight beverage. And the handle on top means you won’t have to wear the pack on your back all the time. $65 at Sears (locations throughout the city, sears.com).

5. The size is right
It doesn’t matter whether you’re a light or heavy packer: This Expand-A-Bag folds out from a petite 9.25 x 8 inches long carry-on into a large duffel with a big inside pocket—great news for those of us who somehow always wind up flying home with a lighter pocket book and double the wardrobe. $40 at Flight 001.