Hakone to Haneda and Itinerary

Hello! I’m leaving for Japan in one week and so far my itinerary is 1 night in Tokyo, 2 nights in Osaka, 3 nights in Kyoto, and 9 nights in Tokyo again. However, I am thinking of changing our time in Tokyo and spending the last night or two in Hakone. However, our flight leaves from Haneda Airport at 2pm on our last day. Would it make sense to spend the last night in Hakone and then go to Haneda early in the morning, or should I play it safe and go back to Tokyo the last night? I also can’t stay in Hakone the beginning of the second Tokyo leg because I’m attending an event at the start of it.

by kayvela