I have used my travel humidors for several months while on extended busing trips without a problem. Throw some boveda's or water pillows in and I am ready to go. That said I have traveled enough and worked at airports to know that I do not want my cigars in checked luggage.
So what I do is use quart sized baggies to triple wrap an old cigar box that I filled with cigars. With a bit of tetris I can get up to 50 in a couple boxes side by side in my computer carryon which is a briefcase type just big enough for a laptop with a 17" screen. Meanwhile the traveldor is packed empty in the checked luggage (in the middle to provide cushion).
As for cutters, put em in your checked baggage to avoid issues. Lighters are a whole other issue. Legal? Yes depending on many factors. Honestly just easier to buy a cheapo when you get there or find a good BOTL to hook you up. This site has helped with that last part.
Good luck and good travels