Please clarify if you are using a default scenery for KMDW or not, because if you use a 3rd party scenery, the first problem is you haven't excluded it from GSX Jetway replacement, something you should always do when you install a new scenery, because GSX Jetway replacement files are only supposed to be used with default sceneries.
In addition to that, I see the #99 error when requesting jetway, which is a panic log from MSFS Simconnect ( it means an "internal Simconnect error" ), and a failure to even get any jetway data from the Navdata API. This is usually caused by having reached the maximum number of objects in a scene, usually caused by your AI traffic too high, especially when using Injection.