The documentation of “chicago” style of page range format says that when numbers are 4 digits long and 3 digits change, use all digits (Rule 5). One of the given example is “1496–1504”. However the referred url “Chicago Manual of Style-rules” is not accessible and this rule is not found in the latest 17th Chicago Manual of Style. Some relevant examples are presented in section 9.61 instead: 1100–1113, 1103–4, 1087–89, 1496–500, 11564–615, 12991–3001 and they follow the previous rules.
Is it necessary to update the specification of “page-range-format = chicago”?
This was a change in Chicago from 15th edition to 16th edition. The table in the spec is the 15th edition rules. We don’t have a Chicago 15th edition style, so I suggest we just update the spec here to conform to the 16th and later table. This would mean to drop the last row. I suggest we use the “Everything else” like @zepinglee suggests, but also keep the numbers in parentheses for maximum clarity.
Interestingly, CMoS17 says: “This system, used by Chicago in essentially this form since the first edition of this manual, is efficient and unambiguous.”