We had a really nice time at Dan's apartment in Chicago. It's walking distance to the Lincoln Park Zoo and the Conservatory. There are some restaurants and coffee shops within half a mile as well.
You can get to downtown Chicago in around 15minutes, which was perfect for us. Since we were renting a car, we used SpotHero to find parking spots in advance.
If you are bringing your own car, then be mindful of the fact you might not always get street parking in front of the apartment. In my experience I was able to find something within a couple of blocks.