Throughout mainly the first season, it can be seen that the headlines do not match the columns themselves.
The first newspapers Gary received are dated November 12th and 13th yet in episode 2, that takes place 1 week later, they talk about the Cubs playing and losing even though the season ends in October. In the 4th episode, Marissa says that Gary received the first paper the same day Mr Snow died, September 28th.
After the pilot, the time line was reset to match the original air date of the show.
A shot used throughout the series is of an accelerated sunrise behind the Chicago skyline, as seen from the lake shore. It has to be a sunset played in reverse, because the shoreline runs roughly north-south, with Lake Michigan to the east.
Sunrise is normally over the lake.