1. I'd have him park by the Howard red-line stop on the northside and take the red-line down to the Addision stop. It's the quickest and least amount of transfers. 2. I always liked going somewhere a little less raucous for a beer or a bite before the games there--Goose Island Brewery on Clark just south of Addison. I really like the Gingerman on Clark north of the park, just past the Metro and Yak-zies. No food there but a great beer selection, laid-back atmosphere and a great jukebox. 3. I lived in Chicago for a long time and I've seen dozens of Brewers-Cubs games there and I've had a problem only once, two years ago in the bleachers when some falling-down drunk middle-aged woman pointedly asked me what the score was (I believe the Brewers were down by a run or two in the 5th inning). Most times people have been pretty friendly, but with both teams competitive that atmosphere might've changed, especially in the bleachers, which tends to attract drunks and morons. 4. I'd just suggest keeping the moral high ground and root for the Brewers (and not against the Cubs, there's a difference) loudly but respectfully. I know we can't stand when Cubs' fans come up to MP and act like dingbats and it was always embrassing to me as a Crew fan when a group of Brewers' fans (almost always a pack of young males) act confrontational and obnoxious. I think the structure of Wrigley is rot--terrible bathrooms and food/beer options, but the view from the grandstands is amazing on a nice afternoon or evening, it's a real jewel.