Yes

you do need a jacket based on the weather in Chicago, IL, USA 2 minutes ago

Why? Because a little drizzle out and just cool enough for a jacket, but not warm enough to ditch it and it's on the windy side!
54°F12°C & Drizzle

Wind is 12 mph19 km/h from the Northwest, gusting to 23 mph37 km/h
October 19
11am53°F12°C13 mph21 km/h NorthwestThunderstorms
12pm52°F11°C18 mph30 km/h NorthwestDrizzle
1pm50°F10°C18 mph29 km/h NorthwestRain
2pm50°F10°C18 mph30 km/h NorthwestRain
3pm49°F10°C18 mph30 km/h NorthwestRain
4pm50°F10°C17 mph27 km/h NorthwestDrizzle
5pm52°F11°C15 mph25 km/h NorthwestDrizzle
6pm53°F12°C15 mph24 km/h NorthwestWindy
7pm54°F12°C15 mph24 km/h NorthwestCloudy
8pm55°F13°C15 mph24 km/h NorthwestMostly Cloudy
9pm56°F14°C14 mph23 km/h NorthwestPartly Cloudy
10pm56°F13°C13 mph21 km/h NorthwestMostly Clear
DateLowHighWindDayNight
October 1947°F8°C60°F16°C15 mph25 km/h from NorthwestRainClear
October 2043°F6°C64°F18°C11 mph18 km/h from SouthClearDrizzle
October 2146°F8°C55°F13°C14 mph22 km/h from WestMostly CloudyCloudy
October 2244°F7°C53°F12°C13 mph20 km/h from WestMostly CloudyPartly Cloudy
October 2340°F4°C53°F12°C8 mph13 km/h from WestMostly ClearMostly Clear
October 2439°F4°C55°F13°C5 mph8 km/h from NorthPartly CloudyMostly Cloudy
October 2543°F6°C55°F13°C7 mph11 km/h from EastMostly CloudyMostly Cloudy

Yes

Low of 43°F6°C, High of 64°F18°C
Wind: 11 mph18 km/h
Precipitation: None

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