I’ve had more laptop cases over the years than I can remember… big cases, small cases, and in-between sized cases. I’ve managed to unload some of my surplus cases via yard sales, craigslist, and The Salvation Army. I kept a Brenthaven backpack style case for my MacBook Pro, and mostly use it for my local urban travels in and around Chicago (oftentimes on public transit). But I felt I needed something better for when I go out of town.

My business travel is relatively infrequent these days — but it isn’t always a business trip that requires me to bring my laptop. I had a decent medium-sized briefcase style case that had a strap on it to slip over the handle on a “roll-aboard” suitcase. The last time I traveled with this combination, I found it to be less than optimal. I was fine with the laptop case while it piggybacked on the handle of the rolling suitcase, but when I checked the suitcase (it was a little too large for carry on), it became a nuisance.

For example, having a traditional briefcase style case with a shoulder strap isn’t too much fun in a long TSA security line. You have two choices: You either sling it over your shoulder (passing it from shoulder to shoulder as time passes) or you try to stand it upright on the floor and kind of shove it with your feet as the line shuffles forward. More often than not, the bag will tip over, not to mention the gunk it picks up from the floor. So I decided to cave in and get a wheeled laptop case. I use the term “cave” because when I was young and foolish, I used to chuckle to myself when I saw people with wheeled laptop cases, and don’t ask me why. Now at the ripe old age of forty, I’ve joined the “wheelies.” And my shoulders (and back) are eternally grateful.

But as I researched which wheeled case to purchase, I had trouble finding one that fit all my requirements. My ideal wheeled case would need to be: preferably not black; able to be used as a traditional shoulder slung case when needed; an assortment of external pockets for smaller items; an area for document folders; and finally — a strap to allow it to piggyback on the handle of a larger rolling suitcase. It was this last requirement that seemed to make my search more of a challenge — most of the rolling cases I saw lacked the strap. I guess manufacturers thought if your laptop case was wheeled, you wouldn’t need to piggyback it to another piece of wheeled luggage. Have you tried rolling two bags at the same time — one in each hand? There is no way to do it without looking like a doofus.

So I was absolutely delighted when I came across the “Level” Carry-On Wheeled Business Tote from High Sierra. It literally hit every one of my requirements, and had a few nice features over and above. It came in several colors, I chose the Amazon/Graphite combination, which matched my sage green Eagle Creek rolling upright case. Most importantly, it had the “piggyback” strap so I could slide it on the handle of other wheeled luggage. When I checked the larger bag, I simply took the High Sierra case off, extended the handle, and presto, no problems (or pains) moving it around the airport. The other things I love about this case include the two zippered corner pockets (on either side of the sliding handle compartment), a zippered swing-out mesh water bottle compartment, and a zippered “quick stash” compartment on the front side of the bag. I looked up the case on eBags.com, and the video on the product page sold me.

This bag isn’t for everyone; many people may find it too large for their needs and tastes. But for somebody looking for a very practical wheeled laptop case, with room to spare, I would highly recommend it.