I stayed at Casa De Ora, Leo's brand new apartment in the historic Kenwood/Hyde Park neighbourhood of Chicago. My experience was fantastic - first and foremost because of Leo's attentiveness and helpful nature as a host.
The apartment is clean and spacious, with a well-equipped kitchen, a comfortable bathroom, and a shaded balcony with an amazing view of downtown chicago.
The neighbourhood is quiet and safe - the apartment is just a few blocks north of Obama's house! Transport links to downtown are a little slow (half an hour on the bus) but Leo gave me lifts to metro stations several times when I needed to get there quickly. Local amenities are limited (two low end supermarkets), but Hyde Park is nearby to the south. Overall this apartment is amazing value and a lovely place to stay, but those travelling without a car and seeking the buzz of the city may wish to look a little further north - e.g. to Leo's other place! :-)