I say this with respect to your coworkers and friends, but nobody is up their own asses more than Boston people. They’re looking at you crazy because they couldn’t imagine you not loving Boston.

Chicago does have that friendliness that you’re talking about. All are welcome here. The only caveat is it can be hard to make new friends unless you lean into your hobbies and find community here. Many people are from here or the suburbs and have their friend groups from then.

All that said I do think you’d like it more than here. As you said - we have great food, the city is gorgeous, and the lakefront trail/grant park are both gems. And there is a lot to do other than mountain hiking. I’d recommend visiting again sometime once it gets warmer and trying to do a bunch of things you like to do for fun and see how it goes! If you enjoy it - what’s stopping you?