I'm glad you enjoy those wonderful Chicago winters, DHH.
Winter in Chicago isn't that bad. Do you think "wow, this is great weather" every day during the winter? No. But the spring, summer, and fall is very enjoyable. The problem with Chicago is that there are no other hackers around (all the tech people work for banks, and end up being as interesting as you'd imagine), and there are no 24-hour coffee shops, at least not near me. Chicago is a good place to be if you want t…
In the words of 37signals -- and Dr. Phil -- get real. Winter is hell in Chicago, summer is a pressure cooker, and fall and spring are tolerable for a few days.
"Isn't that bad" is relative. Weather in the Bay Area is amazingly good. One of three mediterranean climates in the world. There is no comparison.