Chicago or Philly?

I grew up in Jersey and had some exposure to Philadelphia. Currently been living in Chicago for a couple of years, and contemplating Philly as my next home. The two main reasons: A bit milder winter may be nice again, and having my friends close by. The last is important because although I've made a couple of friends here and my fiancee is here too, i still feel "lonely" inside. Hard to explain. I love the city of Chicago though!

Philly hits the mark for its affordability too, which seems on par with Chicago. We have a 2bd condo about a 35 min train ride from downtown CHI and got it for 155k. Decent HOAs too. Philly seems to be in the similar bracket, would anyone else agree?