From looking on the internet it looks like most small dogs fall into the category of city dogs, although none are Chicago specific. Pick what you want. My father always wanted a Cocker Spaniel but never got one.
Just a suggestion but some breeds have inherent problems that have been bred into them along with the positive characteristics people want. Most have to do with breathing or eyes or joints. Choose a breed that looks like something you might want; get online and look at the positive points (is it laid back and not requiring a lot of exercise and roaming room) and the negative (bilateral cataracts, encephalitis, hip dysplasia, etc) and take both into account before picking a partner.
From a personal point of view there are some I would not own because I don’t want to encourage people to keep on breeding them but, again, that is a personal preference.