You are more optimistic on the decision process for the FY17 TIGER grant applications than I am. Perhaps the permanent federal employees will make the decisions as acting agency and department heads, but they will still get guidelines from the political appointees, starting with Secretary Chao, on the process. I think the political need to spread the grants around to Congressional districts and states will keep the grants from being all road and highway projects, but I expect the balance of grants will tilt away from what we saw with the Obama administration. Probably more grants to rural projects. Which, OTOH, may see several freight railroad related rural region projects selected that incidentally improve portions of Amtrak routes.Trump actually likes trains and has been quoted three times as complaining that the US doesn't have a train system like China's. Furthermore he isn't bothering to staff the lower levels of the departments, so it's probably going to be the permanent bureaucracy making the decisions.
Don't be surprised if we still get quite a few "multimodal" TIGER grants, probably for the stuff which is heavily backed by state governments which couldn't find another pot of money for it. They're specifically *not* supposed to be for straight-up highway work. CREATE in Chicago will probably make a push to get grants again, and with the freight component, they might.
As for the Chicago CREATE projects, their best shot for getting significant federal funds is the FASTLANE grant program. FASTLANE is authorized as a 5 year program, so it is not dependent on the annual appropriations. And can provide larger single awards than the TIGER grant program. US DOT had a submission deadline of December 15, 2016 for the $850 million in FY17 funding. There has been no news since then, presumably due to the change in administration and the very slow process in filling the appointed positions.