Yes

you do need a jacket based on the weather in Chicago, IL, USA 4 minutes ago

Why? Because it's pretty chilly!
56°F13°C & Mostly Cloudy

Wind is 11 mph17 km/h from the Southeast, gusting to 14 mph23 km/h
October 16
12pm55°F13°C11 mph18 km/h SoutheastMostly Cloudy
1pm56°F13°C10 mph17 km/h SoutheastMostly Clear
2pm57°F14°C11 mph17 km/h SoutheastMostly Cloudy
3pm58°F14°C9 mph15 km/h SoutheastMostly Clear
4pm60°F16°C8 mph13 km/h SoutheastMostly Clear
5pm62°F17°C8 mph12 km/h SoutheastMostly Clear
6pm64°F18°C7 mph11 km/h SoutheastClear
7pm65°F18°C7 mph11 km/h EastMostly Clear
8pm66°F19°C7 mph11 km/h EastMostly Clear
9pm66°F19°C7 mph11 km/h EastPartly Cloudy
10pm65°F18°C7 mph11 km/h EastPartly Cloudy
11pm63°F17°C7 mph12 km/h EastPartly Cloudy
DateLowHighWindDayNight
October 1655°F13°C66°F19°C8 mph13 km/h from SoutheastMostly ClearPartly Cloudy
October 1755°F13°C72°F22°C10 mph17 km/h from SouthMostly CloudyDrizzle
October 1860°F15°C68°F20°C9 mph14 km/h from SouthwestRainRain
October 1946°F8°C60°F15°C15 mph25 km/h from NorthwestRainClear
October 2043°F6°C66°F19°C11 mph17 km/h from SouthClearRain
October 2142°F6°C55°F13°C16 mph25 km/h from WestRainPartly Cloudy
October 2238°F4°C55°F13°C9 mph15 km/h from WestMostly ClearMostly Cloudy

Yes

Low of 55°F13°C, High of 72°F22°C
Wind: 10 mph17 km/h
Precipitation: None

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