\documentclass{report}
\usepackage{biblatex-chicago}
\usepackage{endnotes}
\let\footnote=\endnote

\renewcommand\enoteheading{\chapter*{\notesname}\mbox{}\par\vskip-\baselineskip}
\counterwithin*{endnote}{chapter}

\usepackage{filecontents}

\begin{filecontents}{report.bib}
@misc{A01,
  author = {Author, A.},
  year = {2001},
  title = {Alpha},
}
@misc{B02,
  author = {Buthor, B.},
  year = {2002},
  title = {Bravo},
}
@misc{C03,
  author = {Cuthor, C.},
  year = {2003},
  title = {Charlie},
}
\end{filecontents}

\addbibresource{report.bib}

\begin{document}

\chapter{Alpha}
Some text \autocite{A01}.

Some text with footnote.\footnote{\autocite{B02}.}

Some text \autocite{C03}.

\theendnotes

\newpage

\chapter{Bravo}
Some text \autocite{A01}.

Some text \footnote{\autocite{B02}.}

\theendnotes

\end{document}