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If by some stroke of luck the Cubbies make the playoffs.... get to Wrigleyville. If they are in town and you can get in to the bleachers ($$$$).. that would be great! If not, watch the game at any local Wrigleyville bar and wait for the party to come to you after the game.
If they are out of town, I would go to a bar in Wrigleyville or Lincoln Park to watch it.
Assuming the Cubbies don't make the playoffs, try to hangout in Bucktown.... there are tons of little bars, cafes, and coffee shops, many with outdoor seating and great peoplewatching. (plus, it is always fun to tell people you ate at the "Earwax Cafe" which doubles as a porn-rental place.
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