Yes

you do need a jacket based on the weather in Chicago, IL, USA 5 minutes ago

Why? Because the cold's there, but it's just a reminder, not an invasion!
41°F5°C & Mostly Clear

Wind is 6 mph9 km/h from the Southeast, gusting to 9 mph15 km/h
October 25
8am41°F5°C7 mph11 km/h SoutheastClear
9am41°F5°C7 mph10 km/h SoutheastClear
10am41°F5°C7 mph11 km/h SoutheastClear
11am41°F5°C7 mph11 km/h SoutheastMostly Clear
12pm41°F5°C7 mph11 km/h SoutheastClear
1pm41°F5°C6 mph10 km/h SouthMostly Cloudy
2pm44°F7°C5 mph8 km/h SoutheastPartly Cloudy
3pm47°F8°C5 mph7 km/h SoutheastMostly Cloudy
4pm51°F10°C6 mph9 km/h EastPartly Cloudy
5pm53°F12°C7 mph10 km/h EastPartly Cloudy
6pm54°F12°C7 mph12 km/h EastMostly Cloudy
7pm54°F12°C7 mph11 km/h EastMostly Cloudy
DateLowHighWindDayNight
October 2540°F4°C55°F13°C6 mph10 km/h from EastMostly CloudyPartly Cloudy
October 2644°F7°C58°F14°C9 mph14 km/h from EastClearClear
October 2744°F7°C55°F13°C12 mph19 km/h from EastMostly ClearPartly Cloudy
October 2845°F7°C56°F13°C10 mph17 km/h from EastMostly CloudyPartly Cloudy
October 2946°F8°C53°F12°C14 mph23 km/h from NortheastPartly CloudyMostly Cloudy
October 3044°F6°C53°F11°C8 mph13 km/h from NorthwestMostly CloudyMostly Cloudy
October 3141°F5°C54°F12°C10 mph17 km/h from WestPartly CloudyPartly Cloudy

Yes

Low of 44°F7°C, High of 58°F15°C
Wind: 9 mph14 km/h
Precipitation: None

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