Strong opinions here:
If you are ready to settle down, buy a house, raise a family in or near a city... Chicago is a safe/comfortable bet.
If you are looking for tech, don't move.
Can you provide more details on WHAT you are looking for in Chicago?
DISCLAIMER: I moved to Chicago about 2 years ago and now i'm back in the bay area.
To expand on this: HN's monthly "Who is hiring?" threads tend to feature the same Chicago-based companies, over and over, with very little change. There's no contest compared to the Bay Area as far as variety is concerned.
It's a great city though, and summers are indeed amazing—in part because the other seasons tend to suck.
The problem I see with Chicago is that there are no unicorns/tech co's that make many people outside of the area say "I really want to move to Chicago to work there!" Doesn't have the same pull as the west coast hubs.
As for tech, I'm a .NET developer and haven't had any issues getting work in the city. Chicago is also a great place to live if you want C++ work because of the financial markets as you have prop trading firms, HFT firms, clearing firms and exchanges all using C++. That same sector also uses .NET as well.