Weather
Chicago, IL Weather Oct. 16–20: 40s Give Way to Near 70
CHICAGO, IL — Chicago faces a cooler start to the weekend before temperatures gradually rebound, bringing sunshine and afternoon highs approaching 70 degrees by Tuesday, Oct. 20.
By Caleb Mercer · 2026-10-14T09:32:06.081Z
CHICAGO, IL — Chicago faces a cooler start to the weekend before temperatures gradually rebound, bringing sunshine and afternoon highs approaching 70 degrees by Tuesday, Oct. 20.
According to the National Weather Service, rain expected Thursday will give way to improving conditions Friday, followed by several days of mostly dry weather and steadily warming temperatures across the city.
The transition comes as a strong area of high pressure moves south from Canada into the central United States, bringing cooler air to parts of the region late this week.
National Weather Service national guidance indicates some locations across the central United States could experience temperature drops of 20 to 25 degrees, with overnight readings approaching freezing in colder areas. However, Chicago's local forecast does not indicate freezing temperatures during the five day period.
Breezy Friday Gives Way to a Sunny Weekend Friday marks the beginning of the change in Chicago, with a high near 56 degrees and breezy conditions following Thursday's rainfall.
Rain chances remain around 30% Friday, mainly before 1 p.m., before partial sunshine develops.
By Friday night, temperatures are expected to fall to around 44 degrees, setting up a cool but increasingly pleasant weekend.
Saturday brings sunshine and a high near 56 degrees, followed by clear skies and an overnight low around 45.
Sunday begins a warming trend, with temperatures reaching approximately 64 degrees under sunny skies.
The combination of sunshine and lighter weather conditions should provide more favorable opportunities for outdoor activities than the rainy conditions expected earlier in the week.
Temperatures Approach 70 by Tuesday The warming trend continues into the new workweek.
Monday's high is expected to reach 65 degrees, with partly sunny skies and an overnight low near 52.
By Tuesday, Chicago could reach 68 degrees under sunny skies, approximately 12 degrees warmer than Friday's projected high.
While the national weather pattern signals a significant cooldown for portions of the central United States, Chicago's extended forecast points toward a relatively brief cool period followed by improving conditions.
The local forecast does not indicate additional rainfall from Saturday through Tuesday.
Five Day Weather Outlook: Oct. 16–20 Temperatures below represent the National Weather Service forecast for Chicago, Illinois, approximately 4 miles northeast of the city center.
Friday, Oct. 16: A 30% chance of rain, mainly before 1 p.m. Partly sunny and breezy, with a high near 56°F. Overnight low around 44°F. Saturday, Oct. 17: Sunny skies with a high near 56°F. Clear overnight, with temperatures falling to approximately 45°F. Sunday, Oct. 18: Sunny and warmer, with a high near 64°F. Partly cloudy overnight, with a low around 50°F. Monday, Oct. 19: Partly sunny, with a high near 65°F. Partly cloudy overnight, with a low around 52°F.