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I mean Chicago has tons and tons of startups, and a "startup culture". For example http://www.1871.com/. But finding startups that money similar to normal companies? Not super easy.

NYC startups even if they paid more, COL is 3x what Chicago is and not that far from SF... so seems a bad place to go if your goal is to "buy a house"

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Well in my personal experience the salary of senior devs in very early-stage startups i've been involved with in NYC get around get about 150K + options (text processing, machine learning, AI-stuff). With 2 incomes and some savings put aside, certainly its affordable, much more so than SF from what i've seen. The dev salary here may be higher because they need to complete with wall street firms, and there are overall less very senior devs in NYC compared to SF.

150k is renting a small apartment in NYC though.

Maybe if you live in Manhattan. If you live out in Bayridge, you can get a 750+ sqft 1-bedroom apartment for $1450/mo. It takes me roughly 35 minutes getting to Soho on the R/N train from 86th st [which is near the end of the R train]

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