Yes

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

Why? Because it's cool. Pleasantly cool, but cool.
52°F11°C & Mostly Clear

Wind is 6 mph9 km/h from the W, gusting to 9 mph14 km/h
September 8
3am51°F11°C6 mph9 km/h WMostly Clear
4am51°F11°C6 mph10 km/h WPartly Cloudy
5am50°F10°C6 mph10 km/h WMostly Clear
6am50°F10°C7 mph11 km/h WPartly Cloudy
7am50°F10°C7 mph11 km/h WClear
8am51°F10°C7 mph11 km/h WClear
9am54°F12°C8 mph12 km/h WClear
10am58°F14°C8 mph12 km/h WMostly Clear
11am62°F17°C8 mph14 km/h WMostly Clear
12pm66°F19°C9 mph14 km/h WMostly Clear
1pm68°F20°C8 mph13 km/h WPartly Cloudy
2pm70°F21°C8 mph13 km/h WPartly Cloudy
DateLowHighWindDayNight
September 850°F10°C73°F23°C8 mph14 km/h from WMostly ClearClear
September 958°F14°C81°F27°C10 mph17 km/h from WClearClear
September 1059°F15°C83°F29°C7 mph11 km/h from SWMostly ClearClear
September 1162°F17°C86°F30°C6 mph9 km/h from SClearClear
September 1264°F18°C85°F30°C6 mph9 km/h from EClearClear
September 1365°F19°C81°F27°C7 mph11 km/h from EMostly ClearPartly Cloudy
September 1464°F18°C76°F25°C8 mph12 km/h from EMostly CloudyPartly Cloudy

Yes

Low of 57°F14°C, High of 81°F27°C
Wind: 10 mph17 km/h
Precipitation: None

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