THIS IS JUST A THEORY: I think he wanted Henry to lead Cal & Abby to that spot so they would have to separate and have Cal find Chloe, while Abby & Henry looked for Wakefield. While they were looking for him, Wakefield had an easier way to kill both Cal & Chloe. I think Henry is in on the whole thing, he just practically screams "I'm guilty!"

I think that he liked the fact that Chloe was scared and so was Cal. He seemed like he wanted Cal to save Chloe, as a game. He liked to see Chloe's face while killing Cal. And he probably would have killed Chloe but he did not have the chance after. Hope this helps. I cried my eyes out at this part its freaking sad

abby said since wakefield killed her dad...he changed the game...so that MAY be why...or maybe it was to lure cal there so wakefield to kill him then her...but abby and henry was there so...he killed them later...and why did chloe jump? she could've went on the other side of the fence. they may have survived that fall...chloe could have survived cuz some people can survive that...and cal may have cuz if the water was ice cold....it would have helped his cut...

Maybe Chloe was wakefeilds kid? He said I alomst got killed for a girl like you.....

i think its because chloe reminded him of abby's mom in some way.

He Didn't Kill Chloe because She Committed Suicide,after saying "You Can't Have Me."

He did not kill her so people would get more involved in the "game" and he could kill them one by one easier

I think he wanted Cal to get her; like a game so he could kill both at the same time. Chole committed suicide first. Very sad. Favorite episode

NO he would have killed her the 2nd time if she didn't jump but he knew she was going to when she said you can't have me

My guess is just for the aspect of psychological torture.
Yes, Wakefield could have just killed Chloe. But keeping her alive in the sewer was just to make everyone wonder if she's alive or dead and feel a pressing need to find her.
It's just like when Madison was kidnapped. She could have just been killed. o.o