President of business operations Crane Kenney said left-field bleachers should be accessible by May 11.
While rooftop owners said the signs mean "lights out" for their business, a judge denied their request.
The owners have asked for a restraining order and say business has suffered due to the construction.
Tickets go on sale Monday for the Sept. 15 concert.
The footage was shot by Jacob Glick, a Ukrainian immigrant who owned cigar stores in Chicago.
Season-ticket holders will have several options as construction on the bleachers continues.
The acclaimed singer will perform at Wrigley Field on Aug. 27.
Proceeds from the fourth annual Woody's Winter Warm Up will benefit the Wood Family Foundation.
Team officials warn the outfield walls may crumble and have to be rebuilt next year when ivy is removed.
Cubs Chairman Tom Ricketts and pitcher Fergie Jenkins will join the tree lighting festivities.
The toy drive, part of the team's 100 Gifts of Service, benefits kids at Lawrence Hall Youth Services.
The Cubs hope to debut new bleachers, five outfield signs and two video boards by Opening Day 2015.
The Cubs want to debut new bleachers, five outfield signs and a bleacher expansion by Opening Day 2015.
Construction crews moved the caretaker's house this week. Excavation work is starting.
The caretaker's house will be restored and brought back to its home at 1053 W. Waveland Ave. by March.
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