Both cities have unique ballpark features. Boston has its Green Monster at Fenway Park. Chicago has its famed ivy on the outfield walls at Wrigley Field. Both have famous watering holes. Fenway has the Cask and Flagon, Chicago has the Cubby Bear. Both cities have baseball TV announcers with their names on food and drink establishments. Boston has Jerry Remy’s Sports Bar and Grill, Chicago has Harry Carray’s, which is an upscale Italian steak house. Michael Jordan has a steak house in Chicago too, and since Larry Bird won’t be opening one anytime soon, this showdown goes to Chicago.