Yes

you do need a jacket based on the weather in Chicago, IL, USA 1 second ago

Why? Because it's cold. simple as that.
43°F6°C & Cloudy

Wind is 6 mph9 km/h from the NE, gusting to 8 mph13 km/h
December 2
2pm43°F6°C6 mph10 km/h NECloudy
3pm43°F6°C6 mph9 km/h NECloudy
4pm42°F6°C6 mph9 km/h NECloudy
5pm42°F5°C6 mph9 km/h NECloudy
6pm41°F5°C5 mph9 km/h NECloudy
7pm41°F5°C5 mph8 km/h NECloudy
8pm41°F5°C5 mph8 km/h NECloudy
9pm41°F5°C5 mph8 km/h ECloudy
10pm41°F5°C5 mph8 km/h ECloudy
11pm40°F5°C5 mph7 km/h ECloudy
December 3
12am40°F5°C5 mph7 km/h SECloudy
1am40°F4°C5 mph9 km/h SECloudy
DateLowHighWindDayNight
December 240°F4°C43°F6°C6 mph9 km/h from NECloudyRain
December 336°F2°C41°F5°C9 mph14 km/h from WDrizzleMostly Cloudy
December 433°F0°C42°F5°C6 mph10 km/h from WPartly CloudyDrizzle
December 535°F1°C40°F4°C10 mph16 km/h from NWCloudyMostly Cloudy
December 632°F-0°C40°F5°C6 mph10 km/h from WMostly CloudyMostly Cloudy
December 736°F2°C52°F11°C10 mph16 km/h from SWPartly CloudyMostly Cloudy
December 841°F5°C52°F11°C11 mph17 km/h from WMostly CloudyMostly Cloudy

Yes

Low of 36°F2°C, High of 41°F5°C
Wind: 9 mph14 km/h
Precipitation: 67% rain

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