I'm pretty sure they have flags for all of their playoff appearances. And, joking aside, there are a decent number of them (2 WS, 8 pennants where they didn't win the WS, 4 division, 1 wild card= 15 playoff appearances). Ok, a lot of them are old but my White Sox only have 9 playoff appearances in the same amount of time (3 WS, 3 other pennants, 3 other division titles). These numbers are all post-1901. I like how the Cubs do their playoff appearances with the flags on the roof; it's a very traditional look. I think they are color coded as well for WS, league, division, WC. The White Sox use to have really nice looking flags above the scoreboard/outfield billboards listing the year and title. Since 2005 they've had banners on the outfield light poles, which actually turned out pretty well. I still think flags are more appropriate for baseball though.