Yes, definitely some neighborhoods of Chicago require either grinding several inches off your teeth or having big ones. I remember as an almost 17 year old getting off the train from the mid-South carrying two very heavy suitcases of my stuff for my Freshman year at college. U of C is on the Southside and the closest station was 63rd St, so rather than going all the way in to the main station and taking a cab or a local train down to campus, I decided to get off at 63rd St and walk. I struggled with my bags off the platform only to discover I was in a neighborhood where a blue eyed blonde almost 17 year old female should not be. A huge black fellow stopped me and said, "Honey, you need to be in a cab . . . NOW" He grabbed my bags, flagged a cab and just about shoved me and my stuff inside. Thus was my introduction to Chicago and its neighborhoods. Six blocks away was Ivory Tower Academia. Although I subsequently went to that station when I would go home or return to school, never again did I do it in a light summer dress looking like a displaced Southern Belle.
And heck, I had taken the train up from the South in the Spring to interview for school and on the way had seen the station marked 63rd St - University of Chicago, so it had seemed kinda odd to ride the train for another 20-30 minutes to get to the main station and then turn around and come back down to campus.