I live in Atlanta, so we have longer summers. It won't start cooling off in the evenings until the humidity drops, and that's usually in late September.
It can still be hot all the way through Halloween, although it can also be freezing at Halloween.
Our colder weather begins in mid November, but it's not that cold. Once December rolls around we get a lot of sub-freezing evenings, but they aren't brutal.
The coldest weather (20s at night) are in January and early February.
Once March hits, we're back to balmy weather, and by the end of May it's hot as heck.
I'll take hot over cold anyday. Hot won't stop me from commuting. Cold might. But since I have never commuted on a bike in the winter (just started this month

), I don't know how I'll like it.
I grew up in San Diego, where even a bad weather day is a good day.