I feel as though if you are at the cubs world series game with your significant other, you have already shelled out plenty of money just to be there, so it has probably got to be something you both enjoy, and in that breath, if it's something you and your significant other enjoy, than what better place to do it than a big moment in your team's history?
Yes, the upcoming Cubs game does seem to be the steal of the season when it comes to sporting event marriage proposals. First of all, there are so many Cubs fans who have waited decades for a Cubs win. Their kids are now grown up and getting married. To have a proposal during the upcoming Cubs game just seems like a multi-generational dream come true for many fans and their offspring.
Especially since it looked like there might not be an upcoming Cubs game. In any event, the person who pops the question there has a giant audience, and no one in the family will ever forget that proposal. You could hardly have a bigger stage for such a huge personal event.
It is a dumb, dumb way to ask someone to marry you. Unless you met at a Cubs game, than maybe. Maybe it would be a good idea in that case. But I think it is kind of silly to ask someone to marry you at a Cubs game just because.