From support today-
I do not know if the Chicago area will get added photogrammetry. This has never been promised. There was supposed to be new imagery added in MSFS / MSFS 2024 by the end of this year, but that has been delayed due to the MSFS 2024 release.
Adding new imagery is not a simple process. All this must go through thorough testing. When it is ready for release, it will be released.