When I was growing up in Massachusetts 60 years ago, it was pronounced as if it were written “Chilly”. Now I hear people pronouncing it as if it were spelled “Chill-Lay”. How do you pronounce it?
If it’s the country: CHEE-lay
If it’s the misspelled meat stew dish: Chill-ly
If it’s the blackface way of saying a young person: CHYL
Not trying to be funny, but context directs pronunciation.
ETA: didn’t vote yet. Please clarify the intent.
The Country. And you are correct, “CHEE-lay” is actually a better representation of how I hear it being pronounced today.
<nitpick> The spicy meat stew is chili, not chile.
Please read what I said.
When I took Spanish, I had a heck of a time doing the rolled “R”. So for practice sake, I pronounce the country as if I am a native, and I add a long rolled “R” as well. Hasta mananna, banana.
“Chile”.
(When doing Hendrix).
I’d say “chilly” and mean the South American county. I’m from the UK FWIW.
Chee-lay. My husband lived there for a couple of years and speaks Spanish with a strong Chilean accent that is noticeable even to my Spanish-challenged self.
Chile, the country: ‘CHEE-lay’
Chile (the fruit) or chili (the stew): ‘chilly’
I think I’ve pronounced it both ways, but probably leaning towards “chill-ay” more often.
If I am paying attention to what I am saying, Chill-lay, but if I’m not really thinking it will probably come out as Chilly. (Not that I talk about the place all that often.)
You put an “R” in Chile? 
Well, different strokes for different folks, I guess!
I say “Chilly” except when I’m being funny, then it’s “Cheee-lay.” And I’m TheChileanBlob, so, you know, I’m right! 
What Zeldar said.
Depends on what language I’m speaking. If I’m speaking English, I say “Chilly,” if I’m speaking Spanish I say, “Chee-leh.”
[tʃaɪɫ] (rhymes with while).
You were thinking about Jimi Hendrix’s song “Voodoo Chile,” weren’t you?
RrrrrrrrrrrrrrrrrrrrrrrrrrrrrShill-Lay!
Thanks for the clarification. I voted.
Chilly. It’s only in recent years that I’ve heard it being pronounced (by politicians and newsreaders) as Chillay. I have no doubt that closer to the correct pronunciation but I’d feel I was being pretentious if I changed now. Ditto Nestle.
Chee-lay