1.When it is sunny, but not warm. Tempratures can range from freezing to chilly.

So-called because Chicagoans, who live under gray skies for about 70% of the year, break out summer clothes at any glimpse of sunshine.

Suprisingly, they are usually quite comfortable in t-shirts when it's 20 degrees Farenheit, as the long, harsh winters give them opportunity to become acclimated to bitter cold.

2. When winter is not quite over, but it's sunny and no longer snowy. Still cold enough for a jacket.
Damn, i left my coat at home because i thought it was warm out, but it's just Chicago t-shirt weather.

I'm so happy it's almost spring! The snow's finally starting to melt, and we've been getting Chicago t-shirt weather instead of blizzards.
by ((Kill)) Hannah March 10, 2006
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