Wheat (Triticum aestivum L.) production is severely threatened by an increase in the frequency of drought events. It is crucial to determine stable and effective morphological, physiological, and associated oxidative stress indicators, to evaluate the drought tolerance of wheat for breeding and cultivation. Therefore, the cultivars Luohan 22 (LH 22, drought−tolerant) and Zhengmai 366 (ZM 366, drought−sensitive) were used as experimental materials to analyze the changes in 12 physiological and biochemical indicators, as well as the yield, when the stress was prolonged to different times. Re-watering after 6 days of drought can effectively alleviate the associated oxidative stress of drought to wheat. The physiological responses of plants were reversible when they were re-watered in the range of 6 to 12 days after drought. The degree of recovery of LH 22 was higher than that of ZM 366. Afterwards, seven indicators, including stomatal conductance, proline, malondialdehyde, soluble sugar, hexokinase, glucose, and the non−photochemical quenching parameter, were screened out to characterize tolerance of wheat to drought using the multivariate statistical analytical method. This study further investigated the method of evaluating and indexing tolerance of wheat to drought, from the physiological and biochemical levels. This study can provide a theoretical basis and reference for the selection of wheat cultivars to breed and cultivate against drought stress.