https://versus.com/en/chicago-vs-toronto , https://www.youtube.com/watch?v=56SCacQEkb4
Of course both are big cities on the edge of big lakes & have cold winters & hot summers.
https://www.linkedin.com/pulse/connected-lakes-exploring-shared-dna-toronto-chicago-george-khalife
https://www.reddit.com/r/toronto/comments/g4o2i7/im_always_bewildered_by_the_similarity_between/
http://www.chicagosistercities.com/sister-cities/toronto-canada/