who he likes to play with? or who does he like play with?
Me resulta difícil traducir; "Con quién...". Thanks!

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Thanks for all answers;-)

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Who does he like to play with? [best choice]
Whom does he like to play with? [very formal]
With whom does he like to play? [very formal]

"who he likes to play with ...." as it stands cannot be a direct question because it has no auxiliary verb to form the interrogative. However, it could be used as an indirect question:
"she doesn't know who(m) he likes to play with, but ...." 
Whom sounds a bit too formal, but not grammatically wrong.
It would be WRONG in the following instance to use the auxiliary  verb:
"she doesn't know who(m) does he play with ...."  
because this is an indirect question and the auxiliary verb 'does' is not required in indirect questions.

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"Who does he like to play with?" (modern English)  OR "with whom does he like to play with?" (old fashioned).   Does this make sense?

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Hello, Ms. Garcia:

Nowadays a few (very few!) people still follow the rule:

WHOM does he like to play with?

With WHOM does he like to play?

(Who = quien) (Whom = con quien)

I think that most Americans would use WHO in your question. 

So if you wish to follow the "old-fashioned" rule, use "whom"; if you wish to speak and write as do most Americans, use "who."

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Who does he like to play with?

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