I used to live in Chicago (Rogers Park).
There's Skyscraper Heels on W. Belmont between Western & Damen, which is a CD-friendly shop (the owner himself is a DQ).
The Payless on N. Broadway shares a lot with a dry-cleaners service and a Walgreens. I shopped there often with no issues.
The entire Edgewater district, as well as N. Halsted between Addison & Fullerton (maybe a bit more south) also has plenty of places to hang out. In particular check out Beatnix (another CD-friendly store).
I'm sure there are other options for stuff to do. Chicago is huge. If not where I am, it's a place I'd definitely like to be.
