I'm skimming through Bug City, and it seems as though all the ways in are pretty much sewn up by the UCAS military, though I'm sure that this is not the case. I was wondering how players who have already visited Chicago (Containment Zone era) managed to effect an entrance?

First group I was in started in Bug City. That was fun. Another group I GMed for were working as disposable assets for KE, got sent in as part of the run. Damned if I can remember the objective though. Had something to do with a kidnapping.

I'd say your best bet to get in is send your resume to Damien Knight, c/o KE Deniable Assets Department. Getting out however is where the REAL trick is going to be, or just surviving while in there depending on where you are in the metaplot timeline.

you can travel to Chicago via train or bus or drive. Then when you are there ... you can try and get into the CZ through the wall. You would need to find some underground contacts. There will always be an underground railroad. someone that has dug tunnels a kilometer long to skirt under the walls.

Much of the wall is just bulldozed houses/buildings. You can climb over ... but there is the risk of getting hurt in the climb. There are towers that keep watch ... but bribing some guards would not be hard to do.

Make sure you bring lots of stuff to barter with when you go in.