For someone that grew up in south Orange County, and never having served in the military, I have nearly died quite a few times (feel free to guess how in the comments). Only once before though was it going to be as a result of a plane crash. Back when I was going to school in New York, I was on one of those little 30 person capacity planes where in upstate New York there was a pretty nasty storm. The plane dropped for a while and everyone on board was freaking out a bit. I however was strangely calm about the whole thing, and sure enough the plane straightened out and things were fine. Plane crashes and me were surprisingly alright.
That was until I was flying back from my humanitarian work in Africa where the 737 I was on was tilted at a 90 degree angle, shook violently, and began a slight nose dive. How did I know it was pretty drastically tilted? Carry-ons in the overhead fell out, and my water bottler tipped over emptying its contents all over the crotch of my pants. I was decidedly less cool with this. Why? Because I was over Texas. Sure, I may have nothing really going on in life, and the Kings were not playing hockey currently, but something about dying above Dallas seemed really, really awful.
I mostly feared that jerks from Texas would toss insults around me, and I'd be unable to retort since I would be, well, dead.
Unfortunately, I ended up with a fate worse than dying in Texas, as the plane landed and I was trapped in Dallas for the foreseeable future. And I had water spilled on my crotch so everyone of course thought I had pissed myself (not this time!). I have been through Texas a few times, and it was always awful. Being there is like having to take the worst dump imaginable, but every bathroom is in use. Then an asshole wearing a cowboy hat and talking with a Texan accent comes over and says, "Move it you long-haired faggot". Thankfully, I escaped Hell on Earth and wound up in San Diego, but not before suffering a plane ride with fat, narrow minded, self-entitled people from Dallas (is there any other type?).
Of the two options, I'd prefer to I die in Boston. It's a nice enough city at times, even if some of the populace is a bunch of douchebags who feel they are the greatest gift god has bestowed on the northeast (when it's clearly Dunkin Donuts). You already know my stance on Chicago. Boston also has an ocean.
However, in terms of myself getting killed Chicago is the safest bet in the entire United States. Probably on par with some South American cities even.
So I want Boston to win, but Chicago will. Neither is desirable, really. The end. Conn Smythe goes to Death (Patrick Kane).