Yes

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

Why? Because it's not very warm out!
54°F12°C & Clear

Wind is 10 mph16 km/h from the Southeast, gusting to 14 mph23 km/h
October 12
12pm54°F12°C11 mph18 km/h SoutheastClear
1pm54°F12°C10 mph17 km/h SoutheastClear
2pm56°F13°C10 mph16 km/h SoutheastClear
3pm57°F14°C10 mph16 km/h SoutheastClear
4pm60°F15°C10 mph15 km/h SoutheastMostly Clear
5pm62°F17°C9 mph15 km/h SoutheastMostly Clear
6pm64°F18°C9 mph14 km/h SoutheastMostly Clear
7pm67°F19°C9 mph14 km/h SoutheastPartly Cloudy
8pm67°F20°C8 mph13 km/h EastPartly Cloudy
9pm67°F19°C8 mph13 km/h EastPartly Cloudy
10pm66°F19°C9 mph14 km/h EastMostly Clear
11pm65°F18°C8 mph13 km/h EastMostly Clear
DateLowHighWindDayNight
October 1254°F12°C67°F20°C9 mph15 km/h from SoutheastMostly ClearPartly Cloudy
October 1353°F12°C72°F22°C4 mph7 km/h from SoutheastMostly CloudyMostly Cloudy
October 1457°F14°C70°F21°C9 mph15 km/h from NorthMostly CloudyMostly Cloudy
October 1554°F12°C63°F17°C9 mph14 km/h from NortheastMostly CloudyPartly Cloudy
October 1651°F11°C65°F19°C5 mph9 km/h from SoutheastPartly CloudyMostly Cloudy
October 1754°F12°C72°F22°C9 mph15 km/h from SouthMostly CloudyDrizzle
October 1857°F14°C72°F22°C10 mph15 km/h from SouthwestRainRain

Yes

Low of 53°F12°C, High of 72°F22°C
Wind: 4 mph7 km/h
Precipitation: None

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