Font's or script have nothing to do with who a chip was made for.
Most old distributors used the same fonts for hotstamps at one time or another.

There are no records available from Treyball.
The CC attributed to Two Brothers Club, Gottage Hills ,IL is questionable IMO. Collectors have a way of putting names to chips. It makes them a lot easier to sell!

"Where do I go from here without going to Cottage Hills , IL. and going through their old books?"

I doubt it would help much if you did. Cottage Hills library should have Newspaper files on microfish and criss cross directories. Not sure what they could do for you unless you have a name or address to start with. If you had that, they should help with history, arrests, etc. But there would not be pictures of the chips.

I have spent hours in libraries and hours on the phone with librarians going through Newspaper files on microfish and criss cross directories with great results, but I had a starting place. IMO you don't have a starting place.

Here is an example of info that can be had if you have a starting place:
Hub mold record HFC, H Combine- Columbus Ohio on the record.
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Howard Fred Combine died 1976, age 69 years (his father was born in Italy; family name Campagnia changed to Combine in US). Both of the addresses on the Mason card were Combine's residence--moved to 834 Seymour in '37.

When the chips were ordered in 1937 he had a billiard hall at 1277 Oak St. in Columbus (the structure in which this address was located no longer exists--see pic). By 1939 he seems to no longer have the billiard hall, but has moved across the street to 1294 Oak where he is the proprietor of a vending machine company (probably including slot machines). He purchases a federal gambling stamp in 1951.

There are a few other Combine chip orders in the Taylor records at preserving gaming history--there may be more,
The second card has 1277 Oak St. as the delivery address.
The chip is hot-stamped "864"--when the chips were ordered in 1940-41, Combine's vending machine company was located at 864 E. Main.
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Also have pictures of the place in 1937 and now.
The above info was gleaned from info attainable on the internet if you have access to the sites.

Here is what you could do. Go to St Louis and search for Treyball heirs. They could possibly have the records. Several sets of records have been found this way.

Collecting old chips is a great thing but without the history , they are only "Little Pieces Of Clay."