A series of 6-aryl-2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)imidazo[2,1-b][1,3,4]thiadiazoles were synthesized through a two-step procedure. The structure of the newly synthesized compounds was confirmed by IR, 1H and 13C NMR, and mass spectra and elemental analyses. All compounds were evaluated for their in vitro antibacterial and antifungal activity against two gram-positive and two gram-negative bacterial strains and one fungal strain. Fluoro-substituted compounds showed comparable biological activity against the tested microorganisms than the -Cl, -Br, and electron-donating groups concerning standard used.