We ended up enjoying our stay in Chicago. There's always a level of unease when you're staying in a location that you know someone else has a key to and could enter at any time. However, we were able (by happen stance) to meet the host, Angenada, and he is extremely friendly and welcoming. He put any safety concerns we may have had as two women traveling alone together at ease.

Maybe it was me overlooking the property details (a real possibility), but we showed up and found that it was a three bedroom and two bath space rather than a two bedroom space as we thought. The third bedroom with an attached bath is clearly used for the host's upkeep of the property and organization of his business product.
In terms of cleanliness, here is what we experienced, all of which can be easily addressed.
-there were dirty dishes in the dishwasher upon arrival.
-there's mold in one of the bedroom closets.
-There was also mold/mildew on the connecting line of caulk that separates the bathtub from the shower wall.
-There was a ring of dried blue toilet cleaner all around the toilet.
-There's small pebbles of what looks like mice droppings behind the couch.
-the friend that I was traveling with saw something small and fast run from near the refrigerator to underneath the stove. She was unsure what it was, but considering we saw potential mouse droppings and a roach trap near the fridge, it may have been one of these types of creatures. This occurred at night after having been gone for a few hours when we flicked on the lights. Potential guests should note that while this might be alarming, you ARE trying to book an Airbnb in an extremely populated city by humans and creatures alike. On the bright side, potential guests should NOT be concerned about the possibility of accidentally bringing home any of these creatures or other bugs from Angenada's property.
As for the amenities:
-we had to buy our own toilet paper. There was only enough left on a roll for a few uses and we did not see any more in the apartment.
-the listing says a baking sheet(s) are provided, but there was no baking sheet we could find. We looked in the oven, in the warming drawer attached to the oven, and in all of the cabinets and drawers. We were unable to cook or seat several food items that we purchased for our trip and were unable to get our money back for them. They went to waste because they did not keep on our long drive home.
-While this isn't an amenity, the upstairs neighbors got home at around 10pm and were pacing until around 2AM for both nights of our stay. It was so loud, that it sounded like they were in the apartment.
-The blinds in the living room are broken, which is a privacy issue. Additionally, they're broken in a spot that allows two different street lights to shine directly into your eyes while you're attempting to watch T.V. at night.
I want to reiterate that Angenada was an extremely kind host and had we notified him of these issues during our stay, I'm confident he would have made an honest effort to fix as many of them as he could. The lockbox was hard to find with the description we were given, but the host was timely and attentive when he received upwards of three phone calls while we were trying to locate the box. He was very flexible in allowing us to check in early and I 100% recommend him as a host, though I want other potential guests to be aware of what you'll experience if changes are not made.