Chicago/ Weather & Environment

Chicago Snags One Last Mild Day Before Halloween Soaker Rolls In

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Published on October 29, 2026
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Chicago is getting one more mild, breezy day before Halloween weekend turns gray and damp. Thursday starts in the low to mid 60s with clouds, climbs to 68, then brings isolated showers and a noticeable cool-down by evening.

The National Weather Service Chicago office expects scattered showers before 3 p.m., with about a 20% chance of rain at any given spot. Winds veering from southwest to northwest at 10 to 15 knots (about 11.5 to 17.3 mph) will help usher in cooler air later in the day, while a stray rumble of thunder cannot be ruled out; no watches, warnings or advisories are in effect, according to the National Weather Service Chicago.

Friday Looks Like The Dry Window

Thursday night should turn mostly clear, with a low around 48. Friday will have extensive cloud cover and be cooler, topping out near 60, giving Chicago a brief break before the next round of rain arrives.

Rain showers are likely after 7 p.m. Friday and are expected to continue into Saturday, when cloudy skies and a high near 60 are in the forecast. The latest update is wetter than Hoodline’s earlier forecast, though showers may taper late Saturday afternoon and leave outdoor Halloween plans with at least a fighting chance.

Sunday Offers A Brief Breather Before A Wet Week

Sunday looks mostly cloudy with a high near 65 and only a slight chance of showers. Rain chances return Monday, followed by likely showers Tuesday, while Wednesday is partly sunny as mild temperatures continue into the first week of November.

For Chicagoans making plans, the forecast is less about a washout than a shifting schedule: enjoy Thursday’s last mild stretch, keep Friday night flexible and have a rain layer ready for Saturday.