Our family trip to Chicago and stay in The Carriage House was fantastic. Douglas is great and very responsive. We had no issues. It was very clean. The later (12:00) and extremely easy check out procedure were a welcome surprise. The apartment is behind another building so it makes you feel like you have a hidden gem know one else knows about. Street parking was pretty easy and could always find a spot. Very quiet street. Very walkable were lots of vintage shops and a good grocery.
This was our first visit to Chicago and we prefer it over NYC. Chicago is easier to navigate, cleaner, kinder, and less congested. Down town is a easy 20 minute drive. If you pay for parking @ Millennium Parking garage on line it is much cheaper. Too much to do so we left plenty for next time!