Yes

you do need a jacket based on the weather in Chicago, IL 60638, USA 1 second ago

Why? Because it's pretty chilly.
50°F10°C & Mostly Clear

Wind is 4 mph6 km/h from the W, gusting to 7 mph11 km/h
September 8
4am50°F10°C4 mph7 km/h WPartly Cloudy
5am49°F9°C4 mph7 km/h WMostly Clear
6am48°F9°C5 mph7 km/h WMostly Clear
7am47°F9°C5 mph8 km/h WClear
8am48°F9°C5 mph8 km/h WClear
9am52°F11°C6 mph9 km/h WClear
10am57°F14°C6 mph10 km/h WMostly Clear
11am62°F16°C8 mph12 km/h WMostly Clear
12pm66°F19°C8 mph13 km/h WMostly Clear
1pm69°F20°C8 mph13 km/h WPartly Cloudy
2pm71°F21°C8 mph13 km/h WPartly Cloudy
3pm72°F22°C8 mph13 km/h WPartly Cloudy
DateLowHighWindDayNight
September 847°F9°C74°F24°C8 mph12 km/h from WMostly ClearClear
September 956°F13°C82°F28°C10 mph15 km/h from WClearClear
September 1057°F14°C86°F30°C7 mph11 km/h from SWMostly ClearClear
September 1159°F15°C88°F31°C6 mph9 km/h from SClearClear
September 1261°F16°C88°F31°C5 mph8 km/h from SEClearPartly Cloudy
September 1364°F18°C83°F28°C6 mph10 km/h from EPartly CloudyMostly Cloudy
September 1464°F18°C79°F26°C6 mph9 km/h from EMostly CloudyMostly Cloudy

Yes

Low of 55°F13°C, High of 82°F28°C
Wind: 10 mph15 km/h
Precipitation: None

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