I have some questions about the people and the environment.
What time of day is it?
What season is it?
Is the weather hot, cold, rainy, windy, or sunny?
Did the squatters have anything in common like, same metahuman race or ethnicity? Age? Sex? Did they carry weapons? Baseball bats or laser canons? Did they act like social rejects out in the dumps because they can't find a social place in Chicago, or did they act like angry exiles that were pissed to be out here? Did they proudly fly any gang-related signs or flags? Did they speak English with an American accent or a British accent or did they not speak English well at all? Were any of them missing any limbs or have any big scars in obvious places? Like claw marks across the face or neck? How did they react to our mode of transport? Like hungry animals waiting to strip any mechanical object within their line of sight, or did they not care about our trans?
lol, sorry, I think too much. But, since you asked, there's some questions. Don't feel obligated to answer them all. 
Time and date is in the first IC post. "October 9th, 2072. 5pm - one and a half hours until twilight." It's orange.

Wind is very light at this time since the heat on the lake and the ground isn't too different. That will change after dark, resulting in a moderate wind coming from the west. This job isn't a time-sensitive thing, so, naturally, the date was chosen with a clear weather forecast in mind.
The squatters you saw were mostly a mix of human and ork. They were armed well enough that you'd expect them to be part of the Union militia, but they weren't a gang. They probably joined the Union back when the former Union leader Catherine Cunningham was the big swinging dick in the Zone - Before the FAB III ate her magic away. You get the feeling that they're still here because they have nowhere else to be.
As an ASIDE: Everyone in the CZ is SINless. Back when they set up the current SIN registry after the Crash of '63, many internal and external factions made sure that as few Zoners as possible made it to the registry points to get a SIN and find their way back into the greater population. Most Zoners were too damaged to leave and get back into society anyway. The general consensus amongst the people of Chicago is that even if you leave, no one ever really gets out of the zone.
Your initial encounter was brief. After hearing your intentions and your offer, they agreed and quickly escorted you to the stairwell. Nothing was said. Those of you with moderate perceptions noticed that the hallway ceilings were lined with det-cord and charges. Seems that they believe in the civilizing force of mutually-assured destruction. Also, lots of faces peering out of slightly-opened doors on the way to the stairwell showed a fighting force of more than enough to cause significant trouble to anyone with an idea to nose around. Some had the gaunt hard look that you'd see in, perhaps, the old-school mujaheddin of Afghanistan. Some had the wiry look and battle scars of pit fighters. Zoners are a hardened people used to very little comfort and regular helpings of grief. They are the 1% of the population who survived. Each one, the hardest, meanest and slyest of 100 peers. You know that they will do or take anything they think they can get away with, and they know that you know this and will have taken precautions against the obvious, like vehicular theft.