To be honest the chances are so damn low, but I'm still hoping for a season 2 also. However, right now your better off reading the light novel considering it's been more than 5 years since it finished airing. So if your considering reading the light novel than start on like volume 6 or 7 since that's where the anime left off, unless you wanna read from the start to see what the anime cut out.
But for now I guess I'll start putting up some of my own opinions: (Btw, everything else written below this part has ABSOLUTELY NOTHING to do with season 2, is just my opinions on what I wished the show had done)
1. I wished the Head Mistress/Academy Director Momoka Shijou was the main heroine personally, because she's actually the type I like and prefer. She's white (look I prefer white skin tone, but I have nothing against other skin color alright? Is just what I prefer), she has blonde hair, she has a childlike height/body, and she's flat (yeah... I actually prefer flat, never knew guys like me existed right?), and has a Tsundere personality (is hard to tell she is a Tsundere if you have no interest in Tsundere and observe them the most when watching anime, but since I love Tsundere it was easy for me to spot it), and she even have a twin-tail hair... Absolutely my type right there. Noticed how I said personally, not everyone so no need to get mad.
2. Come on.. explain how tf the time traveling works! Like I get it but don't get... please.. explain..