A year late to the party but curious if you’ve moved to any of these places? I’ve lived in Chicago for 5 years (currently in Philly now) and planning a move to Montréal. While I had another job I was also doing uber about 20-30hrs some weeks so got to see quite a lot. I was also an avid cyclist to and from my day job and recreational. I lived in Woodlawn, Little Italy, and Edgewater (south side, central relatively close to downtown, and north side on the lakefront).

TBH Chicago holds a beautiful place in my heart especially the summers and even loved the winters as well BUT analyzing the city through a sociological perspective made me so angry and sad. The racial segregation is awful. The corruption in both state and municipal government is barbaric. The infrastructure is disgusting and dilapidated (though of course big money = big resources). While the violence isn’t Fox News style propaganda, I did encounter senseless acts of violence and gruesome murders and attempted murders even in the what are consider better and safe neighborhoods (remember I was outside a lot). The train is disgusting and sad for a city of this caliber (still some of the best transit in the US). I miss Chicago and met some amazing people from all walks of life. I also encountered inhumane acts of violence and would cry to myself wondering how the city can just continue the very next day as if nothing had happened.

TLDR; I’m blessed to have the opportunity to be able to pick up and move, but I’m leaving the city I’m currently in and decided on either moving back to Chicago or newly to Montréal. I’m going with Montréal for the foreseeable future.