Even cities with great transit systems struggle for funding. Chicago has an extensive but old transit system that needs major repairs and upgrades.
As reported by Crain’s Chicago Business, the Illinois State Legislature finally passed addition funding for it, in the form of a quarter-percent sales tax increase for Cook County (to 1.25%) and a half-percent sales tax increase for the neighboring counties (to .75%). While this will bring in more than $400 million per year and allow for long-overdue repairs, its still not enough to make significant upgrades.
A Chicago Tribune opinion piece stated they still rely on 1967-vintage elevated-train designs and buses with odometers that have gone around two or three times. Chicago Metropolis 2020 — a non-profit, business-supported planning organization that has lobbied for increased transit funding — studied the regional economic impact of the capital investments recommended in the RTA strategic plan and found that the return on this public sector investment would be great.