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Winter: F (Nov-Mar) - Blistering cold
Spring: F (Mar-June) - No leaf out till mid may
Summer: B (June-Aug) - Decent, too cool for my liking though. cold evenings
Fall: F (Aug-Nov) - Leaves first show colour change late Aug
Winter: B. Plenty of fine weather, but can get wet spells
Spring: B. Plenty of snow on the hills, but can be changeable
Summer: B. Lovely, but can get chilly nights
Autumn: A. Awesome, uplifting.
Chicago -- and I'm focusing specifically on areas right by the lake and my own personal tastes.
Winter -- D
It is Chicago and it is winter and it would get an F without the caveats. Caveats though are that there are occasional breaks (like this year), and there is good variation between cloudy days and sunny days so it's a good balance between being sunny and uber cold all the time like the Dakotas versus cloudy and snowy all the time like the other side of the lakes. Also a caveat because the city is VERY good at managing winter (aka not having to drive, or shovel snow, plus CTA train timers, and Uber), and it's a built in great traveling season.
Spring -- B+/A-
Cool, refreshing days with lake breezes is a big plus. Days with a clear blue sky and 55 degrees with a breeze off the lake are some of my favorites all year. Oftentimes on the cool side of severe weather fronts so 45 and drizzle beats tornadoes every time.
Summer -- A-
Great season! Great variation between sunny "perfect" days with just about the right number of hot tropical days so that there are some but not usually not too many. Not a big fan of t-storms.
Fall -- A
Many sunny warm days with cool nights. Just about right. November can get chilly but usually not awful.
Far too warm and we're never "safe" from shots of hot, humid air from the Caribbean even in January. Too many 70+ lows. December has been horrid the past five years which sucks majorly.
Spring: F
Too sunny and dry. Too late for winter cold snaps and too early for summer thunderstorms. Sun feels intense especially after winter. Sunglasses are your friend in a South FL spring.
Summer: B+
I love the summer atmosphere with the intense sun and plentiful summer thunderstorms. I love the amount of rain we get and I can appreciate hot, humid weather during summer. Only issue is that nights are too warm for my liking, I prefer lows around 70 F instead of 77-79 F.
Fall: F-
Most frustrating season. Heat and humidity are stubborn to leave, meanwhile places like 200 miles north are seeing lows 20+ degrees colder. I get tired of hot weather in late August and September is still very summer-like. October is faaaaaaaaaaaaaaaaaaaaaar too warm as is November. November can be a pleasant month sometimes but too inconsistent, we see 75 F lows as easily as we see 50 F lows in November. Frustrating.
Winter: F (Nov-Mar) - Blistering cold
Spring: F (Mar-June) - No leaf out till mid may
Summer: B (June-Aug) - Decent, too cool for my liking though. cold evenings
Fall: F (Aug-Nov) - Leaves first show colour change late Aug
May and September in Winnipeg aren't that bad, they're warmer than here
Winter: B (snowy and nice for the most part)
Spring: C (too slow to warm up, but after winter acceptable)
Summer: C (could be a lot worse)
Autumn: D (too cool, too short)
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