My friend and I specifically picked out a place in Wicker Park for our first time in Chicago, since we heard it was a good neighborhood. There are plenty of small businesses within walking distance (check out Penelope's for mid-range designer clothing and Handlebar for good vegetarian food in a divey bar).
Sebastien was able to greet me at his place when I arrived in the city. My friend and I met Dayo, who was a bit shy and scared at first, and barks upon meeting people. But he is such a cute fluffy child that will warm up to you.
Our room and private bathroom was very clean and comfortable. Sebastien is a great host that allows you personal time and space, yet at the same time he's open to chatting and hanging out around his flat. He also has a handmade booklet of places he recommends in the area, which is quite thoughtful.
I recommend staying here if you are planning a visit to Chicago!