Now they are updating the technology that makes the place run, see Chicago’s 911 emergency center to get a $75 million upgrade.
This is just the software that is being upgraded. The structure itself cost $217M when it opened in 1995. One big lesson they learned over the years is that having software developed as a "one-off" for just them is incredibly costly. Making as big a switch as they anticipate doing in 2020 will be a challenge. Just switching from one version of CAD software to another is hard enough.
I think you can assume there will be some glitches along the way.