Yes

you do need a jacket based on the weather in Chicago, IL 60623, USA 1 second ago

Why? Because it's cool. Pleasantly cool, but cool and it's on the windy side!
51°F11°C & Mostly Clear

Wind is 8 mph13 km/h from the East, gusting to 25 mph40 km/h
October 28
2am51°F11°C9 mph15 km/h EastMostly Clear
3am51°F10°C11 mph17 km/h EastMostly Clear
4am49°F9°C10 mph15 km/h EastMostly Clear
5am47°F8°C8 mph13 km/h EastMostly Clear
6am46°F8°C7 mph12 km/h EastPartly Cloudy
7am46°F8°C7 mph11 km/h EastMostly Clear
8am45°F7°C6 mph10 km/h EastClear
9am45°F7°C7 mph11 km/h EastMostly Clear
10am45°F7°C7 mph11 km/h EastMostly Clear
11am44°F7°C7 mph11 km/h EastPartly Cloudy
12pm44°F7°C7 mph12 km/h EastPartly Cloudy
1pm45°F7°C8 mph13 km/h EastMostly Cloudy
DateLowHighWindDayNight
October 2746°F8°C57°F14°C7 mph11 km/h from EastMostly ClearMostly Clear
October 2844°F7°C59°F15°C10 mph16 km/h from EastMostly CloudyPartly Cloudy
October 2945°F7°C55°F13°C14 mph22 km/h from NortheastMostly ClearPartly Cloudy
October 3044°F7°C54°F12°C9 mph15 km/h from NorthPartly CloudyMostly Cloudy
October 3142°F6°C54°F12°C8 mph13 km/h from NorthwestMostly CloudyMostly Cloudy
November 140°F4°C50°F10°C6 mph10 km/h from NorthwestMostly CloudyPartly Cloudy
November 234°F1°C49°F10°C7 mph11 km/h from SouthwestMostly CloudyMostly Cloudy

Yes

Low of 45°F7°C, High of 59°F15°C
Wind: 10 mph16 km/h
Precipitation: None

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