Green’s Dictionary of Slang

1. (US tramp) to arrest, albeit without a specific charge.

1924		G. Henderson Keys to Crookdom 400: Capture. Caught [...] chalked.
1931		Irwin Amer. Tramp and Und. Sl. 49: Chalked. – Detained by the police, often with no definite charge as yet entered against the prisoner. It was formerly the custom to mark with chalk the doors of those cells from which the prisoner was not to be released without special orders.

2. (US) to assess, to identify.

1947

C.S. Montanye ‘Frozen Stiff’ in Popular Detective Mar. 🌐 You chalked it as a gang rub.

3. (US black) to take note of.

1958

C. Himes Real Cool Killers (1969) 107: Shhhh [...] Chalk the walking Jeffs.

4. see chalk off v.²