Yes

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

Why? Because it's pretty chilly and it's super windy outside!
50°F10°C & Windy

Wind is 18 mph29 km/h from the East, gusting to 27 mph44 km/h
October 29
6am50°F10°C18 mph28 km/h EastWindy
7am49°F10°C17 mph28 km/h EastWindy
8am49°F9°C18 mph29 km/h EastWindy
9am48°F9°C18 mph29 km/h EastWindy
10am48°F9°C19 mph31 km/h EastWindy
11am48°F9°C18 mph30 km/h EastWindy
12pm47°F8°C16 mph26 km/h EastWindy
1pm47°F8°C17 mph28 km/h EastWindy
2pm49°F9°C18 mph28 km/h EastWindy
3pm50°F10°C18 mph29 km/h EastWindy
4pm52°F11°C18 mph29 km/h EastWindy
5pm53°F12°C17 mph28 km/h NortheastWindy
DateLowHighWindDayNight
October 2946°F8°C55°F13°C16 mph26 km/h from NortheastWindyMostly Clear
October 3044°F7°C55°F13°C11 mph17 km/h from NorthMostly ClearMostly Cloudy
October 3142°F6°C53°F12°C9 mph15 km/h from WestMostly CloudyMostly Cloudy
November 141°F5°C52°F11°C6 mph9 km/h from NorthwestMostly CloudyPartly Cloudy
November 239°F4°C54°F12°C8 mph13 km/h from SouthwestPartly CloudyPartly Cloudy
November 345°F7°C58°F15°C11 mph17 km/h from WestMostly ClearMostly Clear
November 440°F4°C56°F14°C6 mph10 km/h from WestMostly ClearMostly Clear

Yes

Low of 44°F7°C, High of 55°F13°C
Wind: 11 mph17 km/h
Precipitation: None

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