transpack sidekick pro

Going to Deer Valley in a few weeks and want to carry on my boots. Everything else will get checked. I also will have computer, Ipad, headphones, etc. Which bag do people recommend for this? Outside of this I don't really have use of a boot bag as the hotel is ski on ski off and the same is true...

I have a Kulkea Powder Trekker that I use every time I go to the sloes. But my husband and I are planning a trip to Japan over Xmas (Tokyo and then Niseko) and I'm also looking at a heli trip for next year. I'm a proponent of carrying my boots on the flight, but my Kulkea bag won't fit in the...