Yes

you do need a jacket based on the weather in Chicago, IL, USA 26 seconds ago

Why? Because too cold for just a hoodie, too warm for a parka and it's so windy, your hat has officially retired from your head!
32°F0°C & Cloudy

Wind is 14 mph23 km/h from the Southeast, gusting to 22 mph35 km/h
February 5
8pm32°F-0°C14 mph23 km/h SoutheastCloudy
9pm32°F-0°C15 mph24 km/h SoutheastCloudy
10pm31°F-0°C13 mph21 km/h SoutheastSnow
11pm31°F-0°C11 mph18 km/h SoutheastSnow
February 6
12am31°F-0°C10 mph17 km/h SoutheastSnow
1am31°F-0°C9 mph14 km/h SoutheastSnow
2am31°F-1°C5 mph8 km/h SoutheastCloudy
3am31°F-1°C4 mph6 km/h SouthCloudy
4am31°F-1°C3 mph5 km/h SouthwestCloudy
5am31°F-1°C5 mph7 km/h WestCloudy
6am31°F-0°C6 mph10 km/h WestCloudy
7am32°F-0°C8 mph12 km/h WestMostly Cloudy
DateLowHighWindDayNight
February 526°F-4°C32°F0°C11 mph18 km/h from EastCloudySnow
February 628°F-2°C40°F5°C11 mph18 km/h from WestPartly CloudyPartly Cloudy
February 718°F-8°C29°F-2°C4 mph7 km/h from WestMostly CloudyMostly Cloudy
February 824°F-5°C32°F-0°C9 mph15 km/h from EastHeavy SnowMostly Cloudy
February 922°F-6°C28°F-2°C6 mph10 km/h from NorthwestMostly CloudyMostly Cloudy
February 1019°F-7°C30°F-1°C5 mph9 km/h from NorthwestPartly CloudyMostly Cloudy
February 1117°F-8°C26°F-3°C11 mph18 km/h from NorthCloudyCloudy

Yes

Low of 28°F-2°C, High of 40°F5°C
Wind: 11 mph18 km/h
Precipitation: None

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