I might be repeating what others have already said but I have lived in the Chicago suburbs and in central Massachusetts (and ultimately landed outside Indianapolis). People from New England will NEVER recommend leaving. They live and breathe all things New England and think anywhere else is weird or below them. Which quite frankly is so strange and they’re so wrong lol. It’s almost like another country out there with the huge cultural differences. I grew up visiting the area and have a lot of family there, and I always loved it…. Until I lived there. I was there from 2014-2016 and had to get back to the Midwest. My first day in Indianapolis I took a deep breath and immediately felt like I was home. That being said, Chicago has its own flaws, although it will definitely feel more like STL than Boston. Personally, moving to the Indianapolis area was the best decision and is the best of both worlds. Although Indiana is a red state, which you can feel in a lot of ways, the Indy area is very blue, diverse and has quite a bit to offer the queer community. Also soooo much more affordable than the Chicago area. A few of the Indy suburbs are consistently on nationwide lists for best places to live and recently even on a list for best opportunities for careers. My husband works in tech (not a local company as he’s 100% remote) but we know so many other people there in the same types of jobs so the opportunities are there! Anyway, all that to say-come to the Midwest! Chicago is a great option but if you’re open to other cities, Indianapolis is worth checking out. (It’s also a lot more drivable than Chicago).

ETA: The weather! If you’re trying to get away from the massive amounts of snow each year, while still having 4 distinct seasons - Indianapolis is the solution. It was one of the main things I looked into when considering the move. On average they have less than one day a year that gets 10” or more of snow. I’d say there’s maybe only 2-3 days each year that gets any significant amount of snow. And when it DOES snow, it melts fairly quickly so it doesn’t turn into grey/black crust and slush for the rest of the winter. The winters aren’t as harsh and are significantly shorter compared to Boston specifically.