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This is supposedly fully funded by the Boring Company. No tax money will be put in the project. At least that's what they are saying.

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.