Yes

you do need a jacket based on the weather in Chicago (South Side), Illinois, United States 1 second ago

Why? Because the cold's there, but it's just a reminder, not an invasion!
48°F9°C & Clear

Wind is 8 mph13 km/h from the West, gusting to 17 mph27 km/h
October 31
4pm49°F9°C9 mph14 km/h WestClear
5pm51°F11°C10 mph16 km/h WestClear
6pm53°F12°C11 mph17 km/h WestMostly Clear
7pm54°F12°C10 mph17 km/h WestMostly Clear
8pm55°F13°C10 mph16 km/h WestPartly Cloudy
9pm54°F12°C9 mph14 km/h WestMostly Cloudy
10pm52°F11°C6 mph10 km/h WestMostly Cloudy
11pm50°F10°C4 mph7 km/h WestMostly Cloudy
November 1
12am48°F9°C4 mph6 km/h WestPartly Cloudy
1am47°F8°C5 mph8 km/h WestPartly Cloudy
2am46°F8°C5 mph9 km/h WestPartly Cloudy
3am44°F7°C6 mph10 km/h WestPartly Cloudy
DateLowHighWindDayNight
October 3141°F5°C55°F13°C8 mph13 km/h from WestMostly ClearPartly Cloudy
November 138°F3°C49°F9°C6 mph10 km/h from WestDrizzlePartly Cloudy
November 238°F3°C53°F12°C6 mph9 km/h from SouthwestPartly CloudyPartly Cloudy
November 340°F5°C57°F14°C11 mph17 km/h from WestMostly ClearMostly Clear
November 437°F3°C58°F15°C6 mph10 km/h from SouthwestPartly CloudyMostly Cloudy
November 541°F5°C60°F16°C12 mph20 km/h from WestPartly CloudyClear
November 636°F2°C52°F11°C5 mph8 km/h from SouthPartly CloudyCloudy

Yes

Low of 37°F3°C, High of 49°F10°C
Wind: 6 mph10 km/h
Precipitation: 43% rain

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