I fly every week with my cigars so here is what I suggest:
I would leave the lighter behind since those are prohibited unless they're emptied, put in an approved container and checked. I've brought my cutter everywhere - just not my expensive one because I'm still wary of some overzealous TSA person.
As far as your actual cigars, I wouldn't check them. Even if you pack them well, I've seen luggage take a 10-15 foot fall off the baggage belt, seen them fly off the carts in front of me while being driven around, etc. Plus, the cargo sometimes sits out in the ramp for certain periods of time, subject to the elements. And although I believe innate goodness of people, stuff has been known to disappear from checked luggage. Security won't hassle you for having cigars since enough people travel with them they know what it looks like.
Regards,
Randy