McLuhan was engaged with the University of Chicago for the entire decade of the 1940s. Here are posts describing that engagement in its rough chronological order:

McLuhan’s 1940 review of Adler
Giedion to Nef: “a young scholar of English literature”
McKeon, Gilson and Rorty
McLuhan and Aristotle 4 (Synthesis between Plato and Aristotle)
McLuhan and Aristotle 5 (dualisms in 1944)
McLuhan’s realism 6: dialectics and erudition not enough
The Failure at Chicago
Proposal to Robert Hutchins 1947
Nef on McLuhan’s proposal