Yes

you do need a jacket based on the weather in Chicago, IL 60639, USA 1 second ago

Why? Because the cold's there, but it's just a reminder, not an invasion!
47°F9°C & Mostly Clear

Wind is 4 mph6 km/h from the Northwest, gusting to 8 mph13 km/h
October 31
1am46°F8°C4 mph7 km/h NorthwestMostly Clear
2am45°F7°C5 mph8 km/h WestMostly Clear
3am44°F7°C5 mph9 km/h NorthwestMostly Cloudy
4am44°F6°C5 mph8 km/h NorthwestCloudy
5am43°F6°C5 mph9 km/h NorthwestCloudy
6am43°F6°C6 mph9 km/h WestCloudy
7am43°F6°C7 mph11 km/h WestCloudy
8am43°F6°C7 mph11 km/h NorthwestMostly Cloudy
9am43°F6°C7 mph12 km/h NorthwestMostly Cloudy
10am42°F5°C8 mph12 km/h NorthwestPartly Cloudy
11am41°F5°C8 mph12 km/h NorthwestMostly Clear
12pm40°F5°C8 mph13 km/h WestMostly Clear
DateLowHighWindDayNight
October 3043°F6°C55°F13°C5 mph8 km/h from NorthMostly ClearMostly Cloudy
October 3140°F5°C53°F12°C8 mph14 km/h from WestPartly CloudyPartly Cloudy
November 139°F4°C50°F10°C5 mph8 km/h from WestMostly CloudyPartly Cloudy
November 237°F3°C53°F12°C6 mph10 km/h from SouthwestPartly CloudyMostly Cloudy
November 341°F5°C57°F14°C11 mph18 km/h from WestMostly ClearClear
November 437°F3°C58°F15°C7 mph11 km/h from SouthwestPartly CloudyMostly Cloudy
November 545°F7°C60°F16°C11 mph18 km/h from WestPartly CloudyMostly Clear

Yes

Low of 40°F5°C, High of 53°F12°C
Wind: 8 mph14 km/h
Precipitation: None

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