only ones that look like they might be viable possibilities are ...
Chicago / Chicago Tool Co., 542 W. Jackson Blvd., Chicago, IL / "stampings and pressings" Jan 1922 Automobile Trade Directory /
Chicago / Chicago Tool & Kit Mfg. Co., 161 Whiting, Chicago, IL / "C.T.K." / patent 1644079 Oct 4 1927 William J. O'Neill /
Chicago / Chicago Wrench Co. / bicycle wrench /
I thought I had an ad for a "C.T.K." something, but I cannot find it. The only thing I can find is an ad for a device for securing luggage to a running board. The company sold a bunch of tools to Uncle Sam in 1952, so at least that part of that one is in the right place vintage-wise.
"Chicago Tool Company" just popped up while I was searching for "C.T.K." in a 1922 Automobile Trade Directory. It's quite possible that one might be too early to be considered a viable candidate.
"Chicago Wrench Company" made a little bicycle wrench about which I have zero information. - BK