The biggest problem with Chicago is that it does not have a City Charter, which is the document that spells out the way a City government is supposed to operate:
https://www.discoursemagazine.com/politics/2022/10/14/the-importance-of-city-charters/
Without a charter, it pretty much allows the mayor to do whatever they want and bypass government committees, lawyers, etc. without oversight.
BTW here's the charter for Buffalo:
https://ecode360.com/13550986