OP - As is sometimes the case on FT, what is a simple answer on FT is sometimes overcomplicated by extremely rare exceptions which will not affect the connection times you are booking.

The US does not have formal exit controls. Thus on departure from MCO and ORD, you will not go through any exit border control as one does when departing many countries. If you have an I-94, you no longer drop that off physically.

I take it that you are flying UA. When you check in with UA, UA will for its own purposes, check your passport and visas (if any) and will likely do so again when you board at ORD.

Make certain that you allow enough time to meet the check-in and gate deadlines for your flights. Those are the minimum time to be at the counter (not in line).

Once in a great while, CBP or another federal agency may run checks on departing passengers, usually in the jetbridge. While that may slow boarding somewhat, it won't affect your connection time, because the flight won't leave with passengers in the jetbridge.