Not clear why this is hitting HN today, but these are popular enough in Chicago to be kind of a cliche. No matter how convincing the poster is, I think you'll be disappointed if you plan a trip to visit scenic Galewood.
This was bait enough that I jumped into Google Maps to look at a few random Galewood streets via street view. Obviously very suburban, but looks like it'd make for a nice stroll until you tired of the cookie-cutter layout. Hugh Hefner's childhood home as a bonus.
It’s a total cliché rite of passage to buy one of these when you move to Chicago.
And I am typing that as I look at the Edgewater poster hanging right there over my desk.