NB: I'm not expecting they'd actually do the below. The political downsides of being efficient in your FOI requests are too great to seriously expect somewhere like the Mayor's office would dedicate effort in to achieving it. But document/record management is not some mystical never before done thing.
Somewhere in the 9.5 million dollar budget of the Mayor of Chicago [1] they could squeeze out $20k for a HP Records Manager setup (or any of the dozen competing software packages) and just blindly catalogue all emails in to it. Even without setting up ANY of the business classification features it makes this kind of search trivial.
Perhaps it could come out of the 1.4 million dollars allocated to the "Innovation delivery team" who "Creates and implements new solutions to improve the efficiency of City government.".
Somewhere in the 9.5 million dollar budget of the Mayor of Chicago [1] they could squeeze out $20k for a HP Records Manager setup (or any of the dozen competing software packages) and just blindly catalogue all emails in to it. Even without setting up ANY of the business classification features it makes this kind of search trivial.
Perhaps it could come out of the 1.4 million dollars allocated to the "Innovation delivery team" who "Creates and implements new solutions to improve the efficiency of City government.".
[1] Page 59 Program and Budget Summaries by Department Finance and Administration Program Summary OFFICE OF THE MAYOR (http://www.cityofchicago.org/content/dam/city/depts/obm/supp...)