Just a little bit of perspective for you
Before they won their first title in a long, long, loooooong time, the Boston Red Sox had six consecutive 2nd place finishes behind the Yankees. They also reached the playoffs 4 times in 10 years before overcoming unbelievable odds in 2004. The Red Sox spent hundreds upon hundreds of millions of dollars, they went through five managers, and they won an awful lot of games.
The Cubs have finished better than .500 5 times this decade. This will have been their 4th post season trip since 1998. They've gone through 5 managers this decade, although 2 of those 5 were basically interim skippers once Don Baylor got the well-deserving axe.
In terms of the little successes that come before the big one, I think the Cubs haven't come as close as often as the Red Sox did before they won it all. But that doesn't matter. World Championships aren't built on the backs of last year's team. They're built on the strength of this one and this one only, and while there are some parallels, it doesn't ultimately matter. But essentially I'm only pointing out the comparison between the two for a simple reason - to keep us grounded and reminded that anything can happen, including a bunch of years of coming close.