I think both teams have a LONG WAYS TO GO with the money part of this .
The Sox at least have a realistic choice for a location . The Bears have many hurdles to cross before they even have a chance of building on the lakefront
Yes, money is the key. But this is Chicago, where the Bears rule. They are arguably the most popular sports franchise in town. Baseball is split between North and South. Bulls and Blackhawks have great fans but numbers won't match the Bears. And the Fire is still building its fan base.
Since the Bears are the sports heart of the City... they will get this done one way or another. People will demand it. As for the Sox... that's gonna be more difficult with who owns them and the bad shape the franchise is in right now and with public money not being so eager to join in.