Yes

you do need a jacket based on the weather in Chicago, IL 60657, USA 1 second ago

Why? Because there's a thunderstorm or two nearby and the wind is harsh and biting!
62°F17°C & Isolated Thunderstorms

Wind is 10 mph16 km/h from the South, gusting to 20 mph32 km/h
October 18
11am62°F17°C10 mph16 km/h SouthRain
12pm63°F17°C7 mph11 km/h SouthwestThunderstorms
1pm63°F17°C8 mph13 km/h SouthThunderstorms
2pm63°F17°C10 mph16 km/h SouthwestThunderstorms
3pm64°F18°C11 mph17 km/h SouthwestCloudy
4pm66°F19°C10 mph16 km/h SouthwestCloudy
5pm67°F20°C10 mph17 km/h SouthwestCloudy
6pm69°F21°C10 mph16 km/h SouthwestCloudy
7pm70°F21°C9 mph14 km/h SouthwestCloudy
8pm70°F21°C7 mph11 km/h SouthwestMostly Cloudy
9pm70°F21°C7 mph12 km/h SouthwestCloudy
10pm69°F21°C6 mph10 km/h SouthwestCloudy
DateLowHighWindDayNight
October 1861°F16°C70°F21°C8 mph13 km/h from SouthwestThunderstormsRain
October 1947°F9°C61°F16°C16 mph26 km/h from NorthwestRainClear
October 2043°F6°C64°F18°C10 mph16 km/h from SouthClearDrizzle
October 2146°F8°C54°F12°C15 mph24 km/h from WestWindyDrizzle
October 2242°F6°C53°F12°C13 mph21 km/h from NorthwestMostly CloudyMostly Clear
October 2339°F4°C57°F14°C6 mph9 km/h from WestMostly ClearPartly Cloudy
October 2441°F5°C56°F13°C8 mph13 km/h from SouthCloudyMostly Cloudy

Yes

Low of 47°F9°C, High of 61°F16°C
Wind: 16 mph26 km/h
Precipitation: 92% rain

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