"Do you think it is to late to start? Season starts october 2nd."

No it's not too late.

"Would it work if i just tilled it up and planted? "

The problem with tilling is not only is it a lot of work, you also till up years worth of weed seed that has just been sitting there waiting to get exposed to the sun and germinate. You can spray an area dead with one tenth of the effort of tilling and have a better result.