The city's landmarks commission, which must sign off on any changes to historic structures, was meeting Thursday afternoon to approve the deal.
If accepted, the Cubs could erect a 5,700-square-foot Jumbotron in left field of the 99-year-old ball park and a 650-square-foot sign in right field.
The agreement, reached after weeks of negotiations, underlines the fact that Wrigley, famous for the storied billy goat curse and Babe Ruth's called home run shot, is unlike any stadium in the United States.
Cubs spokesman Julian Green said the Jumbotron is slightly smaller than what the Cubs initially wanted and the right field sign is significantly smaller. The biggest change is that the Jumbotron would be 95-feet wide instead of 100 feet. That means rooftop bleachers across the street will have less obstructed views than the original design.
But the question looms if the latest deal will trigger lawsuits from the owners of the rooftops that peek over the outfield walls.
The Cubs are in the middle of a 20-year revenue-sharing agreement with the owners of the rooftops. It calls for the rooftops to hand over to the Cubs 17 percent of their gross annual revenue that they earn charging people to watch the games from bleachers they've built atop the buildings.
Cutting into their views amounts to a violation of their contracts and will devastate a multimillion-dollar enterprise that relies on a nice clear view of the playing field.
The Cubs have said the rooftop views would be "largely preserved," and have pointed out that most of the massive left-field Jumbotron is in front of one of the few buildings that does not have rooftop bleachers.
The Cubs recently brought in cranes to hoist mock-ups of the signs to see just how much they'd affect the views of the rooftops. The team has made it clear that minimal impact does not mean no impact.
The signs, particularly the Jumbotron, were the most contentious piece of a $500 million renovation puzzle the Cubs have been trying to put together since Ricketts family has owned the team.