The Windy City Showdown continues as Craig Robinson quizzes Nick Offerman about the lengths he would be willing go to for a Cubs World Series win.

Tell us how far you’d go by joining the conversation on Facebook: New Era Cap

See all three Chicago vs. Chicago commercials:

• Round 1 – making fun of Wrigley Field
• Round 2 – how far would you go for a World Series win
• Round 3 – can you sing the national anthem?