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If he flies into LGA, the student can take an Uber to Grand Central (around $35) and then take the Metro North line to New Haven ($16). The train leaves roughly every half hour from Grand Central and takes around 90 minutes to get to New Haven. Very much stress free....
Metro North trains run from Grand Central to New Haven just about every half hour. The last train of the night leaves Grand Central at around 145am and arrives in New Haven around 400am. It's easy to take a cab or Uber from LGA to Grand Central and then hop on the train. Taking the last flight to LGA is always risky for the reason you mentioned. Hope this helps.
I am writing to announce that the Fall 2015 term will end on December 22, 2015, a day earlier than originally planned, after making one adjustment to the fall calendar.
The calendar committee, which is made up of students, administrators, and faculty, had hoped to maintain all the features of the current calendar, including the six-day reading period, the fall recess, and the week-long break at Thanksgiving. To preserve all these features, the committee seriously explored a number of options, including the possibility of starting the academic year one week earlier than originally planned, a suggestion proposed by the Yale College Council.
The committee looked particularly closely at the YCC's request to start the academic year a week early and gathered the necessary information for pursuing this option. It included bringing the freshman counselors and pre-orientation leaders to campus in the middle of August, scheduling annual maintenance during a smaller window of time, and requiring instructors to return to campus two weeks before Labor Day, conflicting with many faculty members' summer research and travel schedules. The committee presented its analysis, of all options, to the vice presidents of the university, who concluded to shorten the reading period by one day, to five days, in the fall term in order to end the semester early and to preserve both fall recess and Thanksgiving break.
The 2015-16 calendar presented particular difficulties due to how the academic calendar is scheduled: fall semesters begin every year on the Wednesday before Labor Day, with no classes held on Labor Day itself. This academic year started on the earliest date possible, August 27. Next year, however, the opening day swings to the opposite extreme, as it does every seven years, to the latest possible date, September 2. Since the 2015-16 academic year is scheduled to begin on September 2, next year's fall-term exam period was originally scheduled to end on December 23. By custom, dorms would have remained open until noon on December 24 (Christmas Eve), and students and staff were understandably concerned about ending so late.
I will be convening a committee and charging it with assessing the fall break and developing a single University academic calendar. I will update you with more details once we have them.