I feel like I hit a lucky streak in Chicago--really great hosting in nice spaces. Oliver really went out of his way to make all the logistics work for my trip. As examples, calculating ample time before the next guest's arrival, he extended my "check-out" time to make it easier to hop on a very long flight back home, and gave VERY detailed and newsy (=content-filled) directions to restaurants, neighborhoods, etc., as well as back-stories about the area, the city. In terms of comfort stuff, multiple nice good towels (have you ever had those ones that are like old toast, and it's obvious the hosts don't actually use the same things themselves? not the case here!), nice breakfast nook, interesting (cf art stuff mentioned in other posts) but not hover-y host/s, all around win-win. The only difficult thing was once daytime parking was hard to find. I suppose that's the tradeoff of living in a vibrant neighborhood with a lot of activity. There is lots of foot traffic in the neighborhood which, as a female traveller, is important to me, so it wasn't really a big deal (and public transit is also very easy, accessible).