If it's a standard Jacobs chuck and you know the chuck number (stamped on the chuck or similar) then it should be simple enough to match up. If not, things get a bit more complex. The link below has some information and there's two more links in that article to even more info. If you still can't figure it out, post back with whatever info you have and maybe we can help further.
drill chuck key sizing
 
Go to a machine tool Supply and get several of the "multi-key" crosses. Each cross has a different size bevel-gear and/or pilot shank. I have two, large & small that fit everything that I have.

Doc :>)
 
After you find your chuck, and if it's for a drill press, wrap a piece of the hook side of some Velcro around the shank, leaving a flag hanging out. Cut a square of the loop side to fit and stick that to the press.
Your chuck will always be where it's supposed to be. (if you put hang it back up) :)
 
I bought one of those and they do not fit any of the chucks I have, either the pilotis wrong or the gear is wrong. And both parts are too small for my drill press chuck. Missplaced the 2 I had when redoing shop. A TSH drill press that is no longer in production, took chuck to Sears and they were able to match me up with a key off a returned bad press. After that I found my keys that had been missplaced. That was after I bought those 4 way keys and they would not fit anything I had.
 
I looked at 4 way keys at HF the last time I was there,neither of those will fit my drill press either.(two drills and both came without keys)
 
And when you get a chuck key, get a magnet and stick it on the front of the drill just below the lid... then stick your key to the magnet, it will be right in front of you.
 

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