Best Rolling Laptop Bag

Now that I work from home, I usually take my laptop with me whenever I travel. Last time I took my laptop, I realized how heavy it was with all the walking I had to do. I actually have a really nice laptop bag. I bought it when I bought my laptop so I could keep it protected when I wasn’t using it which is NEVER! It has lots of compartments that allow me to keep all my travel documents, money and a few personal things in one place so I’m not carrying around my laptop, purse, etc.

Unfortunately, my shoulders and back were in agony before I even boarded my flight. Right before I boarded, I was hanging out in the terminal and walking around checking out the shops. I finally couldn’t take it anymore and I broke down and bought a little cheapo cart thing with wheels for 20 bucks. It had those bungy cords that wrap around the bag to secure it. It did the trick but it was cumbersome. A few times my laptop fell off completely when I rounded a corner. Not to mention that it was one more thing I had to account for. It’s also one more thing I have to store at home in a house that has limited storage.

Travel is Stressful

Traveling can be stressful and hard on the body. You may find yourself sitting for long periods of time but in my experience, there’s an awful lot of walking involved as well–walking to check in, standing in line at security, walking to the gate, walking to a parking lot to get your car; not to mention all the walking involved when you are inside a terminal just going to get a meal or something to read or even a little shopping.

If you have to carry a heavy bag of any kind, it can make your shoulders ache even if you havebest rolling laptop bags the strap across your body to help distribute the weight more evenly. You may find you have a back ache long before you get to sit down and relax on your flight. Putting extra stress on your back can also contribute to sciatica so if you are prone to that at all, a rolling laptop bag could be a better way to ease back pain when traveling–no added pressure!

I’ll be traveling again soon so I’ve been on the lookout for the best rolling laptop bag that has decent wheels on it. If I manage to find a nice laptop bag that also has wheels and has enough compartments to also replace my purse, that’s a winner in my book.

Best Rolling Laptop Bag

So to outline everything I need in order to get the best value for money, here’s the type of bag I’m looking for:

  • Should have wheels
  • Lightweight
  • Space for my laptop
  • Have numerous compartments that will hold my wallet and travel documents
  • A compartment for personal items such as lipstick, mints, maybe my unlocked smart phone
  • Compartment for laptop related items such as mouse and power cord
  • Must meet FAA carry-on requirements so I don’t have to check it in
  • Retractable handle
  • Waterproof and theft proof–not required, but would be nice!
  • Reasonable price

Oscaurt Anti-theft Travel Backpack

I found a laptop bag that is VERY functional and that I love! It might not be beautiful but it ticks all the boxes as far as what I’m looking for. It’s also very affordable.

This laptop bag has zippers that are hidden making it theft resistant. It would be difficult for a thief to randomly try to pull open the zippers because they are under the seams. It also has a USB cable and charging port that can connect to a power bank (not included).

There’s a strap across the back of the bag that allows you to place the bag over the pull up handle on your suitcase making it easier to pull around.


I love the fact that this bag is waterproof, easy to clean, has tons of pockets and storage inside and is very lightweight. While it doesn’t have wheels, it’s very comfortable on my back. It’s not just great for traveling. I use it all the time when I’m meeting clients or working at a coffee shop or Internet cafe.

HollyHOME Rolling Backpack

This bag comes in a few different colors: black, blue, brown and purple. It has an aluminum handle, can fit a 14″ laptop and is easy to clean. Other features include:

  • It’s pretty!
  • It’s lightweight, has tons of compartments and wheels
  • Padded pockets and lined
  • Plenty of storage
  • Retractable handle
  • Water resistant
  • Fits under an airplane seat
  • Price is pretty good

This one also comes with a full refund if you have any problems within 60 days.

The other really cool thing about this bag is that it has a cover for the wheels to keep the wheels from getting dirty. The wheels are unidirectional as well. You can checkout the reviews here.

McKlein L Series EDGEBROOK Leather Laptop Briefcase

This one is really beautiful! It has shock-absorbing foam inside to protect your laptop and will fit a laptop measuring 15.6″-17.” An additional pocket can fit a tablet. Other features include:

  • Made from genuine cowhide leather
  • Zipper compartments inside
  • Expandable handle
  • Available in 5 different colors

Beautiful and functional, this bag also has a locking front pocket to keep your valuable things like your phone and wallet locked but handy to retrieve quickly.

One of the interesting things about this bag is that the company is owned by women! Who best to know what it feels like to carry a laptop bag!

There are many different laptop bags to choose from and finding the best rolling laptop bag doesn’t have to be a big deal. Once you know what you are looking for, finding the best rolling laptop bag to suit your needs should be pretty easy.

Leave a Comment