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Why not SF? That’ll feel closer to Chicago (though transit isn’t nearly as good). Everywhere else you definitely need a car.
Same situation, moving from Chicago to SF in summer :) based on what I’ve seen so far, you’ll definitely need a car if you live outside of downtown.
You need a car in those places
Currently living in Redwood City with no car and it's been mostly fine if you're okay sticking local. However, a car would be nice if you want to explore the rest of the Bay Area. Lyfts/Ubers can get pretty expensive and train service doesn't come often enough to be reliable outside of peak hours. PM me if you want more details.