Because Keio's housing requires you to enter a date of entry on the housing site, I would suggest at least booking your flight relatively early (at the latest, by the end of January). If you start looking early (around 2-3 months before), there will probably be more flexibility with the prices and dates. We got recommended to use a website like Skyscanner, where you can get emails that track the prices for a certain date.
A couple things to be mindful about:
For me, I chose to fly with JAL for my flight to Japan because of the price for the specific dates) and baggage allowances. The flight time didn't matter because I would be arriving with my parents prior to the move-in date. I'm not sure if people book round-trip, but me and Kelsey (another Freeman scholar) decided to go to Korea once our semesters were over. So, we booked our return flight at a different time.
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