This was my first time using airbnb and I have to say that it was a great experience. That was entirely due to our gracious and welcoming hosts.
I stayed at the Pearlman's Guest House with my wife and 8month old daughter.

Their Annex Guest House was spacious, clean, cozy, and had all the amenities of home. If you're going to stay in Chicago, but don't want to be right downtown, I highly recommend you stay here.

The Pearlmans were even nice enough to stock the kitchen with all the basics for breakfast (coffee, juice, bread, cheese, eggs, oatmeal, etc.)

We had a great time in Chicago and having a nice place like this one to go to every night made our visit that much better. We were particularly busy while we were there, so we didn't get a chance to enjoy their beautiful garden. If you have the time, set aside an evening to relax in their garden with a glass of wine.

We'll definitely try to book this location for any of our future trips to Chicago.
Thanks Richard and Cathy! We had a great time.