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If I still lived in Chicago, I would choose May. Springtime in Chicago is the best! But here in San Diego, I pick September. It's still quite nice out, and yet we start getting a break from the 100+ heat! Love it!
Hmmmm, it's a tough choice. Since we just bought a house with a pool, I want the warmth of summer so we can swim every day. But I love the (slightly) cooler temps of fall/winter here. I guess I'd pick October because it can still be super hot here then, but we can also have some nice, cool days, and I'd just have to turn on the heater in the pool, lol.