I never travel with any on board gear with wheels. Anytime they run out of room they go after people boarding with wheels and check them. I had this happen once to me when the plane was getting full and the call came up no more overhead baggage. The first thing they go after is wheeled bags. Also i never use anything to large as too fit on regional jets as well. Today I use a Think Tank Streetwalker Pro version and I believe the Airport Ultralight will work as well. Also if traveling international with a one bag limit you can fit a MBP 15 inch in the front pocket of the Airport Ultralight just use a neoprene case for it so you can pull it in and out without scratching it up. Any mac accessories i either check or fit into side pockets and obviously be aware of your weight. BTW on that flight i walked off and refused to board with checking my roller. They are nice for around town but lately i would never ever use them flying, almost every flight is full now and if your not boarding in front than you could get screwed. Not worth that risk and if the new rule is no wheels than even more so not using one.
In the Streetwalker Pro i can fit DF/P40 and 80 together along with 45D, 28D, 150D. Plus Metz 54 and 5 batteries for back and 2 battery clips . Also with extra room in side pockets if i needed to move batteries to them to fit another lens or 2. Tripod and lighting gets checked