“We are looking at a five-movie storyline," he told the Toronto Sun , listing Peter Parker's debut in Civil War, the current Homecoming, as well as Avengers: Infinity War, the next untitled Avengers film, and finally, Homecoming 2 ("or whatever we end up calling it").
Feige says this will be "an amazing five-story journey for Peter Parker.” That journey will both end the current MCU phase with the untitled Avengers threequel in May of 2019, and kick off the next stage with the Spidey follow up in July the same year.
“In the way that the events of Civil War directly inform the opening of Homecoming and his state of mind as he goes back to high school, so too will the events of the next two Avengers movies as he continues with high school," explains Feige of Spidey's arc.
However, most interestingly, he says that the Homecoming sequel will "usher us into the aftermath and how things proceed from there” when talking about the transition from the last Avengers movie to the second Spider-Man. Does that mean big things will happen with Avengers 3? "Aftermath" is pretty strong word and suggested the upcoming encounter with Thanos and the Infinity War could be messy.
We've already talked about how the MCU needs to kill off some of it's characters to thin the crowd and prepare for future movies. Avengers 3 would be the ideal place to do it. It would certainly add some weight to the current phase if it all went a bit Game of Thrones towards the end.