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Let’s pretend you’ve just been handed $100 million and you have to decide between the urban waterfront giants of Chicagoland or The Bay Area as your new home. Which would you choose and why? Remember, this is supposed to be a FUN discussion as opposed to the traditional heated/pointed debates that typically rage on CD.
Sidenote: I pushed up the amount because of the COL in California and for the higher property taxes in Illinois.
I’m going to go first and say Chicago without question. I’d buy me a nice place somewhere between Near North Side & Lincoln Park or in Wicker Park/Bucktown and enjoy all four seasons for once. Especially a summer on shark free Lake Michigan.
Shark-free swimming is a big plus in my book. In Chicago, if we want to swim with sharks we drive to them.
In San Francisco you'll be able to take a bullet train to LA pretty soon. Like in 30 years. Maybe by then your tall building condo will have sunk down to ground level, making the journey even speedier.
That's ok though, in Chicago you can take a regular train to any number of suburbs that are pretty cool. Like Woodstock where they filmed Groundhog Day, a movie about going crazy in a town where nothing ever changes.
So I guess both cities have trains to nowhere.
Chicago is also blessed with no natural disasters. Unless you count cold so bitter it convinces hundreds of people to scald themselves throwing pots of boiling water into the air, hoping to make snowflakes and get YouTube hits. But that doesn't happen all too frequently. Only like every January.
San Francisco obviously suffers from the threat of earthquakes, and falling into the Pacific Ocean after the big one hits. But everyone knows that so it's priced in. Nothing too earth-shattering there.
Considering all this, I'd definitely choose SF due to the favorable tax treatment from Prop 13.
I would say SF. Nice weather, nice scenery, and cost is really the main issue about moving there.... so if cost wasn't an issue.... I'd love to live there.
There are a lot of people who would absolutely move next week to San Feancisco if only they could actually afford to live there. Virtually nobody thinks that about Chicago.
I'd buy a place in both. I adore Chicago and would absolutely move there if my job took me there. SF is pretty great, too, so I'd just have a place in both.
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In Chicago, if we want to swim with sharks we drive to them. 
