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I am biased, having lived in San Jose and nearby Sunnyvale for nearly three decades combined from 1972-2001. Live just slightly over an hour south now. Usually has better weather than Chicago, especially winters. Know the city very well. Familiar with its attractions, nice areas and the few areas to avoid, etc. Have some family/friends there. Don't know anyone in Chicago. Still have Chicago on bucket list to visit, though.
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