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Both are nice and have a lot of good stuff to do. Most people seem to like San Francisco more, but personally I preferred Chicago. I found that it was easier to get around w/o a car b/c of the El train.
Ballparks: both have jewels of baseball parks: Wrigley and AT&T. AT&T's park may be better, but Wrigley's neighborhood is more fun. I didn't go to a football or basketball game in either place, but Soldier Field and the United Center certainly beat Candlestick.
Art: Chicago with the edge here. The Chi Institue of Art beats the Palace of Legion of Honor and de Young Museum.
Music and Comedy Clubs: Chicago easily. Tons of good blues and the Second city comedy show was great. Not sure of anything comparable in SF.
Parks: I liked Lincoln, Grant/Millenium more than Golden Gate.
Architecture/skyline: Golden Gate bridge is nice, but I prefer the awesome skyscrapers in Chicago.
Wild card: Alcatraz tour in SF was really interesting
If you throw in wine country it is a different story, but for the cities themselves, I liked Chicago better. Obvious caveat is that winter in Chicago sucks, so if we are talking about a winter trip then San Fran gets the win easily based on weather.
I guess Mark Twain and I have something in common.; the coldest winter I ever spent was a summer in San Francisco. Being from Chicago which has fantastic summers, I experienced bone chilling weather weather at Fisherman's wharf, Alcatraz, and my downtown hotel. A friend of mine called while we were walking at the wharf, and we had to duck into one of the shops so my teeth wouldn't chatter. I agree that January and February are pretty bleak, but December and Christmas in Chicago, with the Walnut room at Macy's flagship store and Michigan Avenue are pretty magical, as well as the Christmas trees of the world at the Museum of Science and Industry, and the weather much more in line with the season.
One thing not mentioned here is the clean factor; Chicago is alot cleaner than SF with fewer homeless, making any trip more enjoyable. I agree that the outskirts of Chicago are not as inviting for the tourist, with the exception of quaint towns like Geneva and Long Grove, but they do not match up with Napa, Muir Woods, Sausalito and Carmel. As a transplanted Californian in Chicago, though, I can say that the museums, from the Shedd Aquarium, to the Planatarium, Art Institute, Museum of Science and Industry, Museum of Natural History, etc. are first rate. Throw in second city, Willis Tower, Millenium Park, Navy Pier, and the North side neighborhoods, and you have a pretty good vacation.
Vacationing for me is getting out of the metropolitan I live in & going to another. My vacation goals are to meet hot chicks, go to bars, walk around and see wonderful things, go to museums, enjoy the super gorgeous waterfront, get on a boat & take a tour, check out some shopping specific streets, use the transit to go restaurant hopping, visit some of the architecturally interesting school campuses, see some interesting parks, & of course if it applies go the the tallest skyscraper and just kick it.
Or in Chicago's case, the Signature Room of the Hancock Tower. Incredible view, incredible environment, & incredible place to chillax & have a drink or two.
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SF Summers?
