the acidity or pKa can make a difference in TLC / HPLC - but it depends a lot on mobile phase also (and if you are doing your HPLC with reversed phase columns....)
The set of compounds mixes three factors: acidity (pKa), aromatic vs aliphatic, and F vs H. The problem is that they are not entirely independent.
If you asked me benzene vs cyclohexane (using standard hexane/ethyl acetate solvent system), I would think benzene is more polar (and polarizable) and runs slower. So that is aromatic vs. aliphatic.
If you asked me m-difluorobenzene vs benzene or 1,3-difluorocyclohexane vs cyclohexane, the fluorination can actually make the compounds less polar - I would predict the fluoro compounds run faster. (This is seen the most with perfluorinated compounds - which often have unexpectedly rapid passage through chromatographic systems.)
If it was just the acids, the pKa of cyclohexanecarboxylic is 4.9, benzoic is 4.2, 2,6 difluorobenzoic is 2.85 so the isomer drawn here is somehwere around 2.85-3.0 The 1,3-difluorocyclohexanecarboxylic acid maybe 3.8-4.0? The electronegativity of the F's is transmitted differently through the aliphatic and aromatic skeletons. Based on acidity alone I would predict cyclohexanecarboxylic is fastest, then benzoic, then difluorocyclohexane, then difluorobenzoic.
So the difficulty is this - fluorination by itself can mae Rf larger, but the interaction with the acidity can make Rf smaller. Which factor is more important? Hard to say. If you move to different mobile phases it can make prediction even more difficult.
The technique where it is pretty simple is actually capillary electrophoresis - these are all about the same size so pKa would be about the only factor!