Well, this was a mixed Airbnb experience. Originally, I had carefully picked one of this owner's units to be near some restaurants I liked and a convenient "El" stop (metro). They emailed me at the last minute to ask if I was willing to switch to this one, which I agreed to (even though it's not really in the same neighborhood, Roscoe Village; it's really Bricktown or West Lakeview). There were some great things about it: it's a second-and-third-story duplex unit with pretty good like and a big lovely tree out the back windows (where the dining table is, off the kitchen), and on a quiet street where parking wasn't a problem during our three-day stay. And the beds and pillows were super comfortable -- kudos for providing real down/feather pillows, which few Airbnb owners provide. Plus they had nice toiletries in the bathrooms (though not enough shampoo for more than one or two nights).
But like a lot of Airbnbs that are managed not by individual homeowners but companies renting multiple units, the place feels a bit sterile and careless, and could be better maintained. For example, the thermostat was hanging off the wall, the toilet-paper holder in one bathroom was loose, and the lights above the kitchen island had blown. (In fact, one of them sparked and made a poofing noise when I first turned it on. Despite my texts with the owners, the bulbs weren't changed during our stay.) Plus there was no lamp in one of the bedrooms, just the overhead light.
So, pros and cons. I did appreciate their good communication overall, including a prompt reply at night when I checked in and couldn't find the wifi password (it's inside a big notebook from the owners, near the TV).