Fresh start after long term traveling. Where to?

So I grew up in Ottawa, Canada, but have primarily lived in the US since college. Most of that time I lived in Dallas, spent 7 years there. Starting about a year ago, I quit my job to travel overseas indefinitely. It’s been an incredible experience so far, and I’m starting to consider winding it down and returning to the daily grind. I’m hoping to go back to work with my former employer who said that I could work remotely from anywhere in the US or Canada if I wanted. So I like the idea of taking this opportunity to start off somewhere new.

I’ve been leaning towards Chicago as an option to move to. I visited the city briefly for a long weekend last summer and absolutely loved it. So many great neighborhoods that were vibrant and walkable, people seemed friendly, food was incredible, etc. I also love NYC, but the COL is ridiculous. Chicago felt like a great overall value for such a big city with big city amenities. Also, I don’t mind the cold, kind of looking forward to it after many years in the Texas heat.

I am also considering Toronto as that is close to family and friends in Ottawa, but it just seems very expensive for what it offers. I get the sense Chicago offers a lot more for a similar cost of living or maybe even slightly lower COL.

But I’m curious to hear other peoples perspective. What do you think of Chicago for a single guy in his early 30’s for a fresh start? Is there anywhere else you’d recommend?

Thanks!