Chicago weather has turned wet and windy on Sunday, 20 September 2026, giving residents a noticeably cooler end to the weekend. Rain is affecting the city, while strong winds and lingering water could disrupt journeys and outdoor plans.

Current conditions are near 66°F, or 19°C. Temperatures should peak around 68°F before falling towards 60°F overnight. Anyone travelling should check local conditions because rainfall may leave standing water across vulnerable roads.

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Chicago Weather Remains Unsettled Early This Week

The latest Chicago forecast suggests Monday will bring clouds, occasional sunshine and another possible shower. Chicago temperatures could reach 65°F, with a cooler overnight low near 56°F.

Tuesday should remain breezy. A stray morning shower is possible before clouds begin breaking during the afternoon. Temperatures may struggle to move beyond 63°F.

Conditions remain cloudy on Wednesday, with a daytime high close to 62°F. However, the second half of the week appears brighter. Mostly sunny skies could return on Thursday, followed by temperatures near 67°F on Friday and Saturday.

Rain And Wind Could Affect Travel

Periods of rain in Chicago may reduce visibility and make roads slippery. Drivers should leave additional space, avoid flooded streets and allow more time for their journeys.

The windy conditions could also affect cyclists, pedestrians and lakeside visitors. Gusts frequently feel stronger near Lake Michigan and between tall buildings.

Residents should follow updates from the National Weather Service Chicago if conditions worsen. Weather alerts can change rapidly when heavier showers develop.

Chicago Weather Brings Rain, Wind and Flooding Concerns

Chicago weather has become rainy and windy, bringing cooler temperatures and possible travel disruption across the city. Periods of persistent rainfall may create standing water, particularly near underpasses and other low-lying locations.

Temperatures are expected to remain mild but noticeably cooler than recent days. Residents planning to travel should monitor local forecasts, carry waterproof clothing and allow additional time for journeys during heavier showers.

Weather patterns are also shifting elsewhere, as Los Angeles faces rain before another heat wave, bringing another sharp change in l

Frequently Asked Questions

Is It Raining In Chicago Today?

Yes. Periods of rain and gusty winds are affecting Chicago, with temperatures remaining in the upper 60s.

Will Chicago Experience Flooding?

Lingering water and localised flooding are possible, especially around low-lying roads and poorly drained areas.

When Will Chicago Weather Improve?

Conditions should gradually improve, with mostly sunny skies expected to return by Thursday.

What Will Chicago Temperatures Be This Week?

Daytime highs should generally remain between 62°F and 68°F, with cooler nights in the 50s.