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It's terrible being outside in 100 degree humid weather. You get drenched in sweat doing anything more strenuous than getting the mail.
But it's also terrible being outside in negative windchill weather. I've had my eyeballs start to freeze over. The wind cuts right through you and it's hard being outside longer than 30 minutes because your hands and feet get so cold (even with thick gloves and boots).
Based on this, I'd probably pick the Miami heat. As long as you have water and some shelter from the sun, you'd easily survive. Without a coat in a Chicago winter, you'd die in an hour.
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