Chicago/ Weather & Environment

From Gray Skies to Mild Days: Chicago Heads for a Warm Halloween Week

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Published on October 27, 2026
From Gray Skies to Mild Days: Chicago Heads for a Warm Halloween WeekSource: J. Crocker / Wikimedia Commons

Chicago is waking up to a mild, mostly cloudy Tuesday, with temperatures in the mid-50s early and a forecast high near 63. Rain is unlikely today, setting up a relatively easy day for commutes, errands and outdoor plans before the weather turns more unsettled later this week.

A Warm-Up Hides Under The Clouds

Temperatures should climb through the 60s this afternoon as southeast winds hold around 5 to 10 mph. A lake breeze could keep lakefront neighborhoods a few degrees cooler than inland areas, while the National Weather Service Chicago office says no land-based watches or warnings are in effect.

A Small Craft Advisory for part of the Lake Michigan shore remains in effect through 7 a.m. Tuesday, according to the National Weather Service. For most city residents, though, the main issue is simply a gray sky and a mild afternoon.

Wednesday Looks Like The Week’s Best Weather

Wednesday brings mostly sunny skies and a high near 72, with light southwest winds. Thursday could also reach 73, with showers possible from late Wednesday night into Thursday, and southwest wind gusts may reach 20 mph.

Friday should be cooler, topping out near 69 with a slight chance of afternoon showers. The forecast has shifted from Monday’s breezier setup into a warmer midweek pattern, an update to the outlook previously covered by Hoodline.

Halloween Weekend Brings More Showers

The weekend looks dry beneath mostly cloudy skies. Saturday’s high is forecast near 68, followed by a Sunday high around 72.

Monday currently looks like the wettest day in the extended forecast, with rain showers likely and a high near 66. Rain chances increase later in the extended forecast.