Tom Bihn’s Checkpoint Flyer: My Best Bag Ever

I have an embarrassingly large collection of laptop bags. This isn’t because I am a collector of them as memorabilia. Nor do I have some strange bag fetish. And it isn’t because I have nothing better to spend my money on. It’s because I have had a hard time finding a bag that works well for me under almost all circumstances.

I have tried large and small bags; bags with and without wheels; backbacks and over-the-shoulder models. I feel a bit like Goldilocks as I try each new one out.

And now I think I have found a laptop bag that is “just right.” It’s the Tom Bihn Checkpoint Flyer.

I first came across this bag when someone Tweeted about a different Tom Bihn bag. I had never heard of the company, but I went to check out the recommendation anyway. After looking at the suggested bag, I decided it wasn’t for me, but I was already on the site so I thought I would browse around a bit.

That’s when I came across their Checkpoint Flyer model. Now, I fly every week, so the name itself caught my attention. So I started digging in to it. I was intrigued, but I was concerned about its size — I thought it might be too big for my taste. I was also skeptical about its ability to clear a TSA checkpoint without having to remove the laptop. Finally, the butterfly design gave me pause because it seemed like it could be awkward to use when not at an airport.

Since the price tag on this laptop bag is pretty hefty (my configuration ended up costing $290), I didn’t just dive right in and buy it like I often do with bags. Instead, I did a bit of due diligence. I searched around the web to see what others were saying. I asked for opinions on Twitter. And I read the reviews and watched the videos on the Tom Bihn site.

After my research I was convinced that it was worth a shot. Many folks indicated that TSA really did seem to let it work the way it should. People said they could fit it under the seat in front of them on most airplanes. I measured and it wasn’t much bigger than the fairly compact bag I was using a month ago.

So I ordered it.

And I’m glad I did. This bag has exceeded my expectations. The workmanship is excellent. It fits a ton of stuff in a logical way, but the $30 strap I ordered for it made it feel lighter than my old bag even though I have jammed more into it. Somehow it spreads the weight in a more ergonomic fashion, I think, but I’m no expert. I just know how it feels.

It fits nicely under the seat in front of me, even when I have the often narrower space of an aisle seat. In fact, it is slightly flexible, unlike my smaller but more rigid bag I had been using so it actually does a better job of fitting in tight spaces.

Finally, it does what it advertises: TSA hasn’t given me any hassle over it at all. On my first trip through airport security with it, it did draw extra attention, but as a result of the myriad other gadgets I had in the bag, not because of the laptop. As part of that experience, I realized that if I laid the bag fully flat — essentially in 3 sections rather than just separating the laptop portion from the rest, it would sail through the X-ray machine because there was that much less other electronic gear and wires stacked on top of each other. I have now gone almost a month without any additional scrutiny on my bag which is highly unusual since I used to get a special inspection at least once a week.

Bottom line: this bag is worth the hefty price tag for a very heavy traveler like me. If you’re only taking it to the office and on an occasional airplane ride, it will still be a great bag, but you’ll need to judge for yourself whether it is worth the expense in that situation.

Now I just need a great roller bag. Maybe I’ll have to check out the Eagle Creek Tarmac 22 as recommended by my friends CC Chapman, Chris Brogan, and Mitch Joel.