Yes

you do need a jacket based on the weather in Chicago, IL, USA 3 minutes ago

Why? Because just cool enough for a jacket, but not warm enough to ditch it!
55°F13°C & Clear

Wind is 9 mph15 km/h from the Southeast, gusting to 17 mph28 km/h
October 10
12am55°F13°C9 mph15 km/h SoutheastClear
1am53°F12°C9 mph15 km/h SouthMostly Clear
2am52°F11°C10 mph15 km/h SouthPartly Cloudy
3am50°F10°C9 mph15 km/h SouthMostly Cloudy
4am49°F10°C11 mph18 km/h SouthMostly Clear
5am48°F9°C11 mph18 km/h SouthMostly Clear
6am49°F9°C11 mph18 km/h SouthCloudy
7am48°F9°C9 mph14 km/h SouthMostly Cloudy
8am48°F9°C9 mph15 km/h SouthMostly Cloudy
9am50°F10°C10 mph16 km/h SouthMostly Clear
10am53°F12°C10 mph17 km/h SouthwestMostly Cloudy
11am57°F14°C11 mph17 km/h SouthwestMostly Cloudy
DateLowHighWindDayNight
October 949°F10°C63°F17°C7 mph11 km/h from SoutheastClearMostly Clear
October 1048°F9°C65°F19°C10 mph16 km/h from SouthwestMostly CloudyMostly Clear
October 1152°F11°C65°F18°C7 mph12 km/h from NorthPartly CloudyMostly Clear
October 1252°F11°C66°F19°C7 mph11 km/h from SoutheastMostly ClearMostly Clear
October 1354°F12°C70°F21°C4 mph7 km/h from SoutheastMostly CloudyMostly Cloudy
October 1456°F14°C66°F19°C9 mph14 km/h from NortheastPartly CloudyCloudy
October 1555°F13°C62°F16°C7 mph11 km/h from NortheastMostly CloudyMostly Cloudy

Yes

Low of 48°F9°C, High of 65°F19°C
Wind: 10 mph16 km/h
Precipitation: 12% rain

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