Chicago seems like it has a greater crime problem. Also the gang culture over there is deeply embedded in the city's fabric, going all the way back to the days of Al Capone. However, the demographics there seem like they would be more up my speed. Even though Chicago is very segregated and stratified, there's a large black population there. Toronto, in comparison, is a largely White & Asian city.
I've never been to Chicago, but this is what I know based on the little reading I've done, the news stories I've watched and also stereotypes.
Do most of the blacks in Chicago occupy the underclass or are they mostly well-off (i.e. picket fence in the suburbs, think Kanye West)?