There’s so much to do in NYC, def worth going there first. From there to Philly, it’s also just a $20 bus ticket usually if you want to try to cram both.

NYC, Philly, Chicago in that order.

Do Chicago proper when you have a long weekend - my second fav food city in the US (first is LA)

I’ve been to Boston a few times… it’s okay. Do the other cities first imo before Boston.