Chicago Labor Day Weather: Sunny Skies Monday, Showers Return Midweek With September Cool Down

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CHICAGO, Ill. – Holiday travelers in Chicago can expect smooth conditions for Labor Day Monday, but midweek brings a shift as rain and cooler September air arrive. Drivers heading back on I-90 or Lake Shore Drive may face wet pavement and slower commutes by Wednesday afternoon.

According to the National Weather Service, Chicago will see sunshine and highs near 75 degrees Monday with light east winds. Showers develop late Tuesday night and become likely Wednesday, with the best chance after 1 p.m. Temperatures drop into the low 70s by midweek, signaling the first wave of early September cool air.

Monday’s clear skies will help with outdoor Labor Day plans across Cook County, from neighborhood barbecues to parades. Still, forecasters urge travelers to remain alert for changing conditions, especially those returning to the city midweek. Storms Wednesday could bring gusty winds and slowdowns on major routes including I-55 and I-290.

Overnight lows remain mild through Monday night, hovering in the low 60s, before dipping into the 50s Wednesday night. The pattern points to a noticeable shift from summer heat toward more fall-like conditions.

Residents are advised to take advantage of the dry start to the week, but keep rain gear handy by Wednesday. More showers are possible into Thursday, though drier and slightly warmer air returns by Friday.

Warnings are not currently in effect, but additional advisories may be issued if storms strengthen.

Five Day Forecast for Chicago, Illinois

  • Labor Day Monday: Sunny, high 75, low 63
  • Tuesday: Sunny, high 74, low 63
  • Wednesday: Showers likely after 1 p.m., high 78, low 53
  • Thursday: Mostly sunny, high 74, low 61
  • Friday: Partly sunny, high 68, low 54

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