From what I have found during my months of research, Ann Dunham never applied to the University of Chicago, that was yet another myth passed on.
This sentence found in a really quick search notes there is no documentation that Ann ever applied to University of Chicago:
There is no documentation that she ever applied the University of Chicago.
Found at the following site:
As mentioned this was from a really quick search done before I start another job, if you wish I will find confirmation tomorrow.
Also from some searching today and earlier this evening I found that the student airlift left Kenya September 5, 1959 and spent a period of time(IIRC it as at least two weeks) orienting the students at a central location before they went on to the schools they would be attending. Knowing this means that UH had a late start to their school years.
http://seattletimes.nwsource.com/html/politics/2004334057_obama08m.html
As graduation neared for the class of 1960, Dunham had hoped to join many of her classmates at the University of Washington, and was also accepted to the University of Chicago, according to Obamas memoir, the best-selling Dreams from My Father.
There it is again. University of Chicago. from Dreams -I have not read the book, but Ill take odds that obama never mentioned her uncle was at that University.
Castro was at the UN September, 30, 1960.