Do you need recommendations on places in the US you can work in tech without a car and still enjoy the community? Because I can speak from many years of experience, it's not a difficult life to setup for yourself.
I'd love to hear these recommendations. I know you thrive without a car in New York and Boston, but I would love to hear about other places like that in the US.
Chicago IMHO is just about the only place outside of NYC or Boston that you can live a full life car-free, if you live within the right boundary.
The "Chicagoland Area" is huge and includes swaths of "city" that are suburbs in everything but name. But, if you live within, say, the rough bounds of Rogers Park in the north, to Humboldt Park in the west, to South Loop to the south, a car probably won't be strictly necessary. (With exceptions for some inner neighborhoods that are underserved by transit for historic reasons, like Clybourn Corridor.)
The El subway is great by American standards (but not world standards) and the bus system is comprehensive, with many 24 hours lines. You would almost certainly rely mostly on buses as for historic reasons the El subway was designed to service the inner city loop and not the outlying neighborhoods, so it rarely goes exactly where you want to be, unless where you want to be is always the office.
The bummer is having to wait on a bus when it's very cold or snowing out.
Biking is still quite bad by any standard except the jaundiced American one, but slowly improving after some recent high-profile killings of children on bikes.
Car-free is the way to go within the city of Chicago and now that I live in Southern California, the car-free lifestyle is what I miss most (other than people).
It's hard to get out of town without a car. The commuter rail schedules are focused on people who live in the suburbs and commute to the city, so they aren't really an option. There's good public transit to the airports, however, so if you live car-free in Chicago, New York feels closer than Wisconsin in some ways.
