If I were the mayor of Chicago, I'd take that money and spend it at the airport itself. This line shaves 25 minutes off the travel time for a fairly small subset of people. The gains to be made at the airport are far greater. I get there 25 minutes faster, only to spend the next hour screwing around at the airport. If we: 1. Staffed security such that there was never a line, 2. Staffed the ticket counter such that th…
The $8.5 billion O’Hare Airport expansion project is approved and underway, and it is also funded by the airlines via issuing bonds. Supposedly, no tax money will be involved either.
Block 37 is also designed to serve as a downtown "terminal". Passengers will go through security and check in luggages before they board the trains.
I don't know the regulations, but installing double ended jet bridges doesn't sound that easy to me. It's probably something FAA has to approve. Staffing issues at the ticket counter and security is also outside of the mayor's jurisdiction. It's decided by the airlines themselves, TSA, and the organization that runs the O'hare airport.