What strikes you as being very different?
Weather. Culture. Little things like that. 
How about the subway and bus system? I consider Chicago’s good.
I should have posted this in the Chicago threads.
Can’t speak to the efficiency of San Jose’s bus system other than to say it exists. But in terms of subways, in the Bay Area it primarily functions as a regional inter-city distributor. San Jose may get a BART ( Bay Area Rapid Transit ) extension by 2018. Note the “a” as in singular. About the only places where there is any density of stations for internal city commuting is downtown San Francisco and that is just four in a line. It’s not at all like the New York system or as I remember Chicago’s ( those memories are a bit hazy, as I haven’t been in Chicago in decades )
San Jose is far too spread out for mass transit to work well. That said, the VTA bus and lightrail system do as good a job as I think could be expected. BART is really a city-to-city express train, not a “normal” mass transit system. We do have CalTrain that runs slowly and expensively up to S.F. (where all the culture is).
San Jose is wonderfully diverse; lots of ethnic restaurants for the adventurous.
The biggest thing to me is the weather. It’s absolutely perfect. It’s like it’s a nice day every day (constant marine inversion layer), yet we still get occational rain, and can make a short drive for snow in winter. Rarely does it get too hot, and it’s not dry like a desert. You don’t appreciate it for a few years.
Downsides? It’s not really a city, not much of a downtown. Just a gigantic suburban sprawl that calls itself the same place, with all the good and bad that comes it. Very little culture, it gets sucked away to the City By The Bay.
Besides buses San Francisco has Muni, which I’ve only ridden a few times. New York has far more and better subways but nothing like that.
I could theoretically get from home in Fremont to Santa Clara where I work by public transportation, but it would take forever. There are however two light rail stations several blocks from where I work, so if I picked a house in a different place it might be easier.
As for weather, I went to the U of I in Champaign-Urbana - and weather in the Bay Area is a lot, lot, lot better.
Can anyone comment on San Jose’s desire to increase their public transportation system capacity in the future? One thing I really dug about Chicago was how you didn’t really need a car to live properly.
Like I said, Everything is incredibly spread out in San Jose and the surrounding cities, and so our public transit is run at the county level*. I haven’t heard of any realistic plans to expand. They recently shifted some of the budget from the traditional bus routes to a more local model, at least. Unless you carefully plan where you live and work, it’s tough to go without a car. I have friends who do it with the aid of a bike; the nice weather makes it possible year-round, but it is time consuming.
*: VTA isn’t run by the county or city directly, it’s an independent agency that works with local governments.