Recent forecasts from the National Weather Service indicate a frontal passage shifting Chicago from warm southwest flow to cooler northerly winds on October 14, with daytime highs near 66–68°F and overnight lows in the mid to upper 50s under increasing clouds and a chance of showers. This air-mass change, following several days of 80°F+ readings, creates the main uncertainty for the daily minimum, as timing of the wind shift, cloud cover, and any precipitation will influence how much radiational cooling occurs overnight. Ensemble model spreads remain notable two days out, with some guidance keeping readings milder near 60°F while others allow brief dips toward the mid-50s depending on frontal speed and boundary-layer mixing. Historical October averages near 47°F provide context but hold limited weight given the current warm pattern. Updated NWS point forecasts and next model cycles will likely refine the range ahead of market resolution.