Chilling stress inhibits the growth of okra (Abelmoschus esculentus L.), reduces its overall agricultural yield, and deteriorates fruit quality. Therefore, it is crucial to elucidate the mechanism through which okra plants respond to chilling stress. This study investigates the molecular mechanisms of chilling tolerance by comparing the transcriptome and metabolome of chilling-tolerant (Ae182) and chilling-sensitive (Ae171) okra varieties. We found that Ae182 exhibits higher antioxidant enzyme activities, including SOD, POD, CAT, and APX, suggesting it mitigates oxidative stress more effectively than Ae171. Metabolomics analysis revealed that Ae182 produces higher levels of jasmonic acid (JA) and JA-isoleucine (JA-Ile) under chilling stress, potentially activating genes that alleviate oxidative damage. Additionally, integrated analyses identified key transcription factors, such as AP2, BHLH, and MYB, associated with JA and chilling stress. These findings provide candidate genes for further research on chilling resistance in okra.