"Esterification" is a pretty broad term - is it alcohol and acid (Fischer), alcohol and acid chloride, alcohol and anhydride?
If it is Fischer - not going to completion anyway.
For alcohol/acid chloride reactions... if done stoichiometrically (1:1), the alcohol hydroxyl ought to be gone in IR. The carbonyl will shift but it can be hard to be sure .
Alcohol and anhydride - side product is carboxylic acid and this makes both hydroxyl and carbonyl hard to interpret.
There are some reactions where IR is a good quick diagnostic, but esterification isn't a very good example.