The Brief Chicago will see highs near 80 today with a slight chance of morning showers and afternoon storms. Cooler weather moves in Wednesday with highs in the low 70s and lingering rain. Skies clear by Friday, bringing sunny conditions and highs in the upper 70s through the weekend. Today the Chicago area will have highs around 80 degrees under partly sunny skies. Highs are looking to reach the upper 70s/ about 80 degrees on Saturday and Sunday.