In a follow up to this photo post, Sam Spratlin (also here and here) was kind enough to write:
i was on your blog whilst doing some random searching and i saw your post about the mural off damen and lake... it was painted by a guy named jeff zimmerman... he has done a number of other ones in various chicago neighborhoods... the subject matter of each is location-specific... he takes pics of residents and puts them in the work... he also paints a lot of paintings of ice cream trucks... keep an eye out, i'm sure he will have another gallery show sometime in the future.
A little google search led to Jeff Zimmerman's page
Thanks, Sam!
here's the mural, click for larger version:
The proper name is Top of the World.