Honestly, it's been a while (about a year and half) since we made checkmates. So I'll do my best to remember how it went.
We had 4 locations.
Ellie's house (not really Ellie's house -- some house on the Upper West Side)
Ellie's school (the language school on the 9th floor, above the training center)
Park in LES (used as 4 different locations)
Chess Tournament - UCB Office lobby.
(plus we quickly shot Ellie walking down the street in front of UCB offices)
We spent about 3-5 hours at each location. We shot it in 1 full day and 2 half days.
Will Hines handled most of the pre-production (casting, locations, costumes). He and I and Sean Clements talked about those movie trailers (Step Up, Save the Last Dance, The Cutting Edge, etc.) and I watched them repeatedly to get the look we wanted. When editing the video, I continued to watch those videos repeatedly, which helped maintain the style.
It was a great time to make. I'm glad people like it so much.