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The summer climate difference between Chicago and Detroit is negligible. Chicago is a little further south so it is probably marginally warmer on average. But there can be a "lake effect" at times in the parts of Chicago along Lake Michigan, where it is cooler and cloudier than a short distance inland. Detroit is not immediately on any of the Great Lakes, so this type of micro-climate would be less of a factor there.
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In the summer time it is more similar, but Chicago definitely feels more humid than Detroit in the summer. In the winters, I find Chicago more difficult because its much windier and lake effect isn't as pronounced in Detroit as it is in Chicago.
All in all, if I had to pick one for climate reasons, Detroit easily. Its winters are as cold but not as difficult. Its summers are less humid.
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