Have Cubs fans suffered longer than Indians fans? In terms of years without a title, certainly. In terms of World Series appearances, most definitely -- the Indians have been in four of them since the Cubs last made it in 1945, with Cleveland's most recent title coming in 1948.
Chicago and Cleveland have both enjoyed titles in other sports, most recently the Cavaliers taking the NBA crown in June and snapping their city's 52-year title drought. Chicago has had the Blackhawks, the Michael Jordan Bulls and the 1985 Bears. But Cubs fans in particular not only have gone 108 years without a title, but have endured 11 years of White Sox fans lording their 2005 championship over them.
As someone who lives right in the belly of the beast, let me tell you: It definitely happens. Let's see how the Cubs and Indians match up. This assumes the Indians have Corey Kluber healthy -- he left Monday's game with right groin tightness. If Kluber's injury is serious, the Cubs are unlikely to see the Indians at all..