Fourteen different Achillea species were extracted using the Soxhlet apparatus with dichloromethane and then methanol as solvents. The obtained dichloromethane and methanolic extracts were analyzed using thin-layer chromatography (TLC) and high-performance thin-layer chromatography (HPTLC) to obtain fingerprint profiles. The first chromatographic system consisted of silica gel as adsorbent, a mixture of toluene—ethyl acetate—formic acid (5:4.9:0.1, v/v) as the mobile phase and anisaldehyde as the derivatization reagent. The second adsorbent was cyano (CN) silica gel with non-aqueous (2-propanol and n-heptane [5:5, v/v], both for dichloromethane and methanolic extracts) and aqueous (methanol and water [6:4, v/v] for dichloromethane extracts and methanol and water [4:6, v/v] for methanolic extracts) mobile phases. Anisaldehyde (for dichloromethane extracts) and Naturstoff (for methanolic extracts) derivatization reagents were used. The obtained chromatograms were processed to obtain selected images using the ImageJ program. The similarity between the studied Achillea species was confirmed using the chemometric methods (principal component analysis [PCA], similarity, and distance measures).