Is there any program you are particularly interested in?
I'm a Chicago native, in a Chicago medical school and the only Chicago programs I interviewed at are West Suburban, Northwestern, and will do McNeal.
West Sub: Top choice in Chicago. FQHC's, international experience, research with Northwestern, heavy OB, a ton of fellowships in house (MCH is my interest), academic experience with medical students and work with Loyola University, workload is just right, not too cushy but not Ventura hours. Worse part is no EMR in hospital, not enough peds (on par for FM programs), no trauma (again par for urban FM program).
Northwestern: IMO, will be the best program in 10 years, but as of now, program is too new. They do have interesting aspect in terms of leadership, politics, and research with strong academic affiliation yet community based. Going next year, you would not have the full class and a lot of the doctors at the hospital are not yet resident friendly. You have to be super motivated to be here. More outpatient based compared to West sub, which IMO is easier to pick up if you don't get in residency.
McNeal: Have not yet interviewed and may cancel. Sister program of West Sub, but not as strong, but cushier.