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.
And I am typing that as I look at the Edgewater poster hanging right there over my desk.
And also, didn't realize he released a bunch of cool fonts, too: https://tomato-giraffe-jpm4.squarespace.com/fonts.