Traveling on Airplane with 5 Year Old

Even if a 5 year old child is pulling their own wheelie-suit case... they do not walk as fast as adults. And in a "crowd" as there often is at an airport, they are not as fast as the adult.
Hence, you will probably have to help him.
And it depends on how heavy, his bag will be.
Heavy bags, wheels or not, are hard for little kids to carry or pull.
And it also depends on how long the distance is that they have to walk, at the same time, while pulling or carrying their bag. Or if going up or down stairs, etc.

My kids have wheelie school bags.
It gets full of stuff. It gets heavy.
Sometimes my 5 year old needs help.

I always just put their stuff in with mine but for the plane I bought them a backpack with tons of pockets in it. In the backpack I had their comfort stuff but in the pockets had lots of cool, new cheap stuff. Like in one pocket would be candy, maybe a S.'s sucker or Sweet Tarts, another might be new crayons and coloring books, another might be a Barbie for my daughter or something sports related for my son. You get the idea. Anyway, they were only allowed to grab one pocket a hour. It sure made the trip a lot more enjoyable!
Good luck!
PS: When my kid's were little I used to bring a bunch of Sees suckers for the people around me. That way if my kid's acted up, the people were more forgiving!

Get him a rolling backpack for the plane (pack an extra set of clothes, socks and shoes for him in this one) along with his snacks/toys/books/dvd player or whatever goes with you into the cabin. He can roll it or wear it, but pack the rest of his clothes and things w/ yours.

I got my DD her own suitcase on wheels last year when she was 3.5. It was a child sized one and we only filled it with her "in flight entertainment" (toys, snacks, books, etc.) so it was not too heavy. I always put her clothes in my own checked suitcase.
She INSISTED on pulling it herself for both trips we took... and some of the airports were BIG. We did always have enough time to get to the gate.
Make sure it's easy to pull, stable (doesn't tip easily), don't make it too heavy.and give yourself plenty of time... and it should be fine

At 5....I was probably still trying to push my guy in a stroller through the airport. It is a long walk. I would check luggage and let him carry a small backpack with stuff for plane.

Mine has pulled his own little suitcase since he was 4. I only had to help him on the escalators. However, I will point out that there was no clothing in his suitcase, only his toys! Not sure he would have been so willing to pull it if clothes were in there.

Get him a small one for a few toys and things to do on the plane. Target carries them for kids and they fit under the seat in front of you. They also have the back pack kind with wheels so if he doesn’t pull it he can wear it.

Why do you want him to carry his own bag? It's just easier to put his stuff in with yours and consolidate. That being said - you'd be surprised at what they can do. I traveled with 3 kids by myself - all needing car seats, etc. And the only way I was able to do that was because my 5 year old helped out by wheeling our medium sized checked back (which weighed more than him).

Check em. I had a carry on and both of my kids (3 and 8) had carry ons. it was a hassle.

If you have a backless booster seat, you can take it on the plane. it will fit under the seat in front of you. Otherwise, just do backpacks for the plane.

We've travled with our boys a lot and my youngest did not start taking care of his own suitcase until about age 8. He had his own small backpack with his carry on activities.

M