When a CSL date variable contains a date range spanning two years, both years are always rendered in full — e.g., 2021–2026. However, Chicago style (CMOS 18 §9.63, §9.66) requires condensed inclusive numbers for year ranges, e.g., 2021–26.
CSL already handles this well for page numbers via the page-range-format attribute on cs:style, which supports Chicago-style abbreviation rules. But there is no equivalent mechanism for date ranges.
But styles that use year-range-format aren’t valid CSL 1.0.2 and therefore won’t validate.
I do think it’s worth thinking about how to get straightforward things like this into the CSL spec so that the official repo can accept styles that use them, but I’ll start a new thread for that.
One suggestion on dates, and date formatting config, if there is an effort to evolve CSL going forward: adopt EDTF as the standard date format. It’s a very well-designed, and standardized, extension of ISO 8601, with features useful for bibliographic rendering: ranges, uncertain and approximate dates, seasons.
It also has solid library support (though it’s not hard to parse). Here’s a JS one, and is the standard format for biblatex.
On styling, in my EDTF-based implementation (linked above) I decided to cover a wider range of date ranges than just years; it handles also examples like “May-June, 2013” (localized; so Spanish gets “mayo a junio, 2013”), etc.