These are great testaments so you should feel pretty good about flying your dog to BOS! If he's never flown before, I recommend getting his crate (be sure to check the size required - larger is okay but smaller will result in refusal to carry) 2-3 weeks in advance. Put in a blanket, etc. and then put in treats so that he gets used to going into the crate and then start shutting the door for a while - stay close by at first and then go away but return fairly quickly and then a bit longer each time. Get it up to a couple of hours if you can. That way he'll be sure you're coming back for him even if you go away and he's shut in the crate. Of course, this is all unnecessary if you crate him at home as a routine thing. Be aware, too, of having a toy in the crate that could be destroyed and swallowed if he becomes stressed.
I love the crates that are on wheels for ease of moving the animal in the crate and they do a double duty when stacked as a "boat" for pulling luggage in leaving a hand free to hold the leash. My pups ride happily in the crates as well.
Don't forget to put your dog's name where it can be seen as well as putting an extra meal or two with feeding instructions on the outside of the crate (most travel crates I've used have a compartment with a closing lid on the outside) - makes it easy for airline staff to feed him should a flight go tech or some other delay occur).
Hope it all goes well!