Many, many, many.....,.got the idea~years ago we lived in a rental complex that allowed pets. There was an extra deposit required and an additional $25 monthly charge. If I recall correctly there was also a MAX weight of under 35 lbs. I do believe that the city of Chicago is very welcoming to pet owners. Although I don't live in downtown Chicago I go there often for work as does my husband and we both see plenty of owners walking their dogs. He drives all over Chicago and loves to give me Yorkie sightings~what they are wearing, full coat/short coat, where they were spotted, it's just so sweet when he does this
There are also plenty of dog parks to be found as well.