I traveled from Indianapolis to Chicago for the Tool concert at the United Center. The Airbnb location is on the West side of Chicago, which some people say is not the greatest. But it was not that different from Indy, other than things being more spread out. Chicago is a bigger city. The people whom I met were pretty warm and friendly, despite how cold it was. Chicago is a cool city, from my experience.
What I really loved about the experience was how public transportation is easy and convenient. A bus every 10 - 15 minutes, and David's place is close by many route options (I used route 20). I had no problem getting around where I needed to go. If there's ever a bus problem in Indy, you're probably waiting 30 minutes to an hour. Also, buses run later at night, so if you're at a concert or game, you're fine.
I highly recommend David's place. I wasn't there long, kind of in and out. But the location is great, David's house is nice, David and the people living there are nice and easy going, and plus there is an urban farm, which I unfortunately didn't have time to look at very much. But, hey, I was there for a concert.
Thank you, David. If I'm ever in the Windy City again, I'll try to stay at your place.