Greetings Dave:
You might want to contact a local forest preserve district in the greater Chicagoland area for research access. IL-DNR sites are another possibility. IL-DNR research forms are available upon contacting IL-DNR headquarters in Springfield, IL.
Time of year for pollen collection depends on species and probably weather related phenomena. I'm sure the USDA Forest Service has published literature on pine pollen collection:
http://treesearch.fs.fed.us/
Best of luck!