Yes

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

Why? Because it's quite chilly!
45°F7°C & Mostly Clear

Wind is 7 mph12 km/h from the Northwest, gusting to 14 mph22 km/h
October 24
1am45°F7°C8 mph12 km/h NorthwestMostly Clear
2am44°F7°C8 mph12 km/h NorthwestClear
3am43°F6°C8 mph13 km/h NorthwestMostly Clear
4am42°F6°C8 mph12 km/h NorthwestClear
5am41°F5°C8 mph12 km/h NorthwestClear
6am40°F5°C8 mph13 km/h NorthwestClear
7am39°F4°C8 mph13 km/h NorthwestClear
8am39°F4°C7 mph11 km/h NorthwestClear
9am38°F4°C7 mph11 km/h NorthwestMostly Clear
10am38°F3°C7 mph11 km/h NorthwestMostly Clear
11am37°F3°C7 mph11 km/h NorthwestMostly Clear
12pm37°F3°C7 mph11 km/h NorthwestMostly Clear
DateLowHighWindDayNight
October 2340°F4°C53°F11°C8 mph13 km/h from NorthwestMostly ClearMostly Clear
October 2437°F3°C53°F12°C5 mph8 km/h from NorthwestClearMostly Clear
October 2538°F3°C54°F12°C6 mph9 km/h from SoutheastMostly CloudyMostly Cloudy
October 2644°F7°C59°F15°C9 mph15 km/h from EastPartly CloudyPartly Cloudy
October 2744°F7°C56°F13°C11 mph18 km/h from EastMostly CloudyPartly Cloudy
October 2844°F7°C53°F11°C11 mph18 km/h from EastDrizzleDrizzle
October 2943°F6°C52°F11°C10 mph15 km/h from NortheastMostly CloudyPartly Cloudy

Yes

Low of 37°F3°C, High of 53°F12°C
Wind: 5 mph8 km/h
Precipitation: None

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