yes they can reincarnate treat your chao very good don't lose in races or battles and bring it to the school a lot and you should be fine! Reincarnate it 2 times and then the 3rd time it'll be an angel chao!
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There is no limit on how many times a chao can reincarnate.
It takes about 3-5 hours for a chao to reincarnate, so it would take 6-10 hours for it to reincarnate twice. This is taken from the game Sonic Adventure 2 Battle.
3 to 4 hours
Give any chao it's OWN broken egg shell after giving the chao a few skelaton dogs and it will put it on. Now reincarnate the chao twice with the shell on the whole time and after the second reincarnation, it will be a full egg chao(I think). A lot of people say you can only do it with some sort of cheat but I'm pretty sure what I just said works. Good luck. I am actually trying it right now.
To make a Chaos Chao you have to reincarnate your Chao at least twice. After that, give it 1 of each out of all 21 animals (Note: Do not give them Chaos Drives!). Yes, you can feed your Chao too. If you want it to be an Angel Chaos Chao, raise it with any Hero character: Sonic, Tails, or Knuckles. If you want it to be a Devil Chaos Chao, raise it with any Dark character: Shadow, Eggman, or Rouge. If you want it to be a Light Chao, raise it with a mixture between the Hero and Dark characters and keep it Neutral. When it evolves, it should be a Chaos Chao. Hope that helped! :]