In education, both schools and universities, Chicagoland would compare very favorably with Bay Area (stepkid went to schools in both; entirely unimpressed with BA schools).
In job opportunities at FAANG-type companies Bay Area obviously comes out ahead,but for the vast majority of people both in and out of high tech Chicago both has jobs and is actually affordable and salaries are lower by a far lesser amount than the cost of living, at least if you believe all of the comparison sites like Numbeo. In my personal experience I've had much more money left over in Chicago, working for as Chicago company than working for one in Sunnyvale, and that's even before adding up intangibles of better (well, for the USA, anyway) public transit, better museums, theaters, etc. etc.
On climate BA might win on paper, but personally I like to have actual seasons.