[[ Sadly, as much as I adore the ship (and I’ve written Akatsuki period ItaKisa before), no.
Not if we’re talking just pure canon timeline. RP is a different thing– you can make small or big changes or let things go off on a tangent. But strictly canon? It’s not gonna happen. If we just ignore the fact that statistically, Itachi’s likely just straight, Itachi was never focused on romance anyways.
Izumi could never get much out of him, and it was only during her death that he gave her what he wanted, and even then it was only in her mind.
Itachi simply focuses too hard on one goal and everything else gets put on the side. Romance would be treated as a distraction, and why would he willingly go looking for romance when he is planning for Sasuke to kill him?
This isn’t to say “don’t write it”, because do write it, I love the pairing and I love writing it. But I’m going to be realistic and admit it’s not going to happen in any truly canon instance. He’s simply too focused. He’s planning to die. ]]

