It is extremely unlikely that any amount of tech investment in Chicago would make 1000/mo apartments hard to find. Chicago is enormous, and has underinvested, relatively low-density neighborhoods stretching for multiples of the dimensions of San Francisco.

Logan Square apartments would get more expensive, but the market would respond to that the way it did with Lincoln Park, Wicker Park, Bucktown, and Ukranian Village: by gentrifying westward into Humboldt Park, Hermosa, and Belmont-Cragin.

We have a lot of excess housing stock from the rust belt days and can build a lot more towers(not sitting on fault lines).

Meh, it doesn't have the geographic limits that you get on the coast. The only geographical feature hemming in the city is the lake. You have essentially unlimited space to expand in all other directions. It would be hard to get skyrocketing rents outside of the immediate downtown area.

But mostly Chicago just sucks. Its all the shitty parts of the midwest without any of the good ones. What you really want is Indianapolis, Columbus, Minneapolis, Louisville, etc...