One of the very unique and historic things about the Cubs and Wrigley Field is that it is a neighborhood park with local residents living very close to the park with rooftop buildings outside of the field with a view into the action on Addison St. and Sheffield Ave. For years, people have been going up to the rooftops of these buidlings to watch the games. It is difficult to get a historical perspective about the Wrigley Rooftops since these were private residences, but back in the early days (1900's through the 1980's). There are old photos of early games at Wrigley Field (formerly known as Weeghman Park) that you can see people on the rooftops as far back as the 1910's. Ironically, the park that the Cubs played in prior to Wrigley Field, West Side Grounds, was also a neighborhood park that had rooftops with a view inside to watch the game.
Fast forward to today and most, if not all of the rooftops with a view
of Wrigley Field are now run as businesses with grandstands, full menu
and alcohol. Rooftop tickets for Cubs game are typically sold in
groups of 10 or more with the cost of the ticket including unlimited
food and alcohol. Prolonged legal battles have led to the Cubs getting a
share of the revenue of all of the rooftop locations.
A highly recommended book to learn more about the the Wrigley Rooftops, Wrigley Field and the neighborhood known as "Wrigleyvile" is a book called "living the Dream" by Jim Mcardle. Mcardle was on the staff for Chicago Cubs Vineline magazine. The book is actually about him taking a year off from Vine Line and writing all about the 2008 Cubs season which was the 100th year since the Cubs won the World Series. As a Cubs fan himself, he had hoped that the season would end with a World Series victory, however a solid Cubs team won 97 games, winning the NL central but lost in the first playoff series with a very frustrating 3-0 sweep by the Los Angeles Dodgers.
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