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It its "Yale" vs UChicago, so of course there is the strife between prestigue and what your gut tells you is a better fit...New Haven is kind of a ****hole (http://my.xfinity.com/slideshow/news-mostdangerouscitiesinamerica/8/). That isn't to say you shouldn't go there (I lived in Baltimore for 4 years and actually enjoyed a lot about the city despite its problems). But you should know it isn't a great city.
And based on the above list, you liked UChicago better.
Assign each school heads or tails, flip a coin- you'll know what result you hope for when it's in the air..or if there is a slight twinge of disappointment with the result.