You don't live in the city of Chicago, & it's not as easy to get TV stations in the city limits as it is in the suburbs. Mark lives in Chicago, & it's densely populated.
For the most part, reception will be better when someone is located closer to the transmitters, not farther.
I have easily received WWME-LD in downtown Chicago using a portable digital TV. Plus, I've watched WWME-LD from a home on the northside of Chicago (the home had an analog TV hooked up to a converter box with rabbit ears, the room was on the first floor of a 2 story home, and the only window in the room faces north which is the opposite direction of the transmitter).
Here's a link that says: "Today, with it's signal transmitted from the top of the Sears Tower, WWME-TV is the most powerful low power television station in the nation."
I would think that some other low-powers exist across the country that go out just as far. But certainly this was not the case when WWME-CA was an analog only operation, using the same channel number as a full power CBS station from Freeport, Illinois.
http://chicagomediahub.com/broadcast/television/42-television/404-wwme-tv23.html