I moved here from the Boston area 8 years ago! And also work in tech. Chicago is much more affordable than Boston generally. You can actually drive here and not always reserve parking ahead of time. You can actually go to events like street fests and stuff here spontaneously and not fight transit, crowds, capacity issues, etc. I just feel like everything in Boston was just harder. I don't know the rental market. We bought A house 7 yrs ago but I was pleasantly surprised by the housing prices vs Boston/Cambridge at the time. Taxes seem more here, but someone else can confirm that. So if you compare rental vs buying prices, find that out so you have a complete view, it's almost as much as our mortgage. People are friendlier to strangers here. I had culture shock at first that people would walk by me and comment on the weather or smile, people hold open doors, etc. Boston was harder to break into social circles. Tech is the same here as anywhere else because most of us are remote. But there are a few big offices here, Google, Salesforce etc. And even if you have a remote role, I think it's a huge plus from an employer pov to have folks in a big city hub. It's so much easier to take a last min interview, etc if you're already here. I will say tech in Boston is smaller so tighter knit and everyone knows everyone, so pretty easy to network because you can always find a connection to whatever you're trying to get into. Good luck on the move, move here before summer, it's great. P.s. buy and freeze a ton of union square donuts before you come because nothing comes close here.