Yes

you do need a jacket based on the weather in Chicago, IL 60629, USA 1 second ago

Why? Because just cool enough for a jacket, but not warm enough to ditch it!
57°F14°C & Cloudy

Wind is 9 mph15 km/h from the East, gusting to 16 mph25 km/h
October 28
6pm57°F14°C10 mph15 km/h EastCloudy
7pm59°F15°C10 mph15 km/h EastCloudy
8pm60°F15°C10 mph15 km/h EastCloudy
9pm59°F15°C10 mph16 km/h EastPartly Cloudy
10pm58°F14°C10 mph16 km/h EastCloudy
11pm57°F14°C10 mph16 km/h EastCloudy
October 29
12am56°F13°C10 mph17 km/h EastCloudy
1am54°F12°C12 mph19 km/h EastCloudy
2am53°F11°C13 mph20 km/h EastCloudy
3am51°F11°C12 mph20 km/h EastCloudy
4am50°F10°C12 mph19 km/h EastCloudy
5am49°F9°C11 mph18 km/h EastCloudy
DateLowHighWindDayNight
October 2845°F7°C60°F15°C8 mph13 km/h from EastMostly CloudyMostly Cloudy
October 2945°F7°C55°F13°C14 mph22 km/h from NortheastMostly ClearMostly Clear
October 3044°F6°C55°F13°C9 mph15 km/h from NorthPartly CloudyMostly Cloudy
October 3142°F5°C53°F12°C8 mph13 km/h from WestMostly CloudyMostly Cloudy
November 141°F5°C51°F11°C6 mph9 km/h from NorthwestMostly CloudyMostly Cloudy
November 237°F3°C52°F11°C8 mph12 km/h from SouthwestPartly CloudyPartly Cloudy
November 342°F6°C56°F14°C14 mph22 km/h from WestPartly CloudyMostly Clear

Yes

Low of 45°F7°C, High of 55°F13°C
Wind: 14 mph22 km/h
Precipitation: None

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