Running backyard drainage outlet to street

I have a drainage system in my backyard and it currently runs to the rear of the lot into a ditch. There are a few issues that are leading me to leave most of it in place, but instead route it along the side of my house to the street out front.

My question is, I have a sidewalk and everything between the sidewalk and the street is city property. Can I route a pipe under the sidewalk, chip out a section of curb along the side of the street, and route the water here? I plan to patch the outlet of the pipe with cement to smooth out the curb. I see where people have done this with swimming pools and the like around the neighborhood. Is a permit required to do this?

ETA: There are no covenant restrictions where I live