My favorite summer place is Summerfest in Milwaukee by Lake Michigan. It lasts 11 days ( June 30 -July 10 in 2005)http://www.summerfest.com/
It's only about $10 to get in, and for that you have access to about 10 stages with many genres of music. There's always a headliner (Tom Petty, Santana, Tim McGraw, etc.) which needs an extra ticket, but it's usually more fun just to roam the other stages while eating and drinking.
And the diverse music attracts a diverse crowd of people too. Nice grounds, reasonable prices, easy to get to. Much better than taste of Chicago!
What do you like about Milwaukee's Summerfest?
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I Like the grounds and the eggplant at the Venice Club, but prefer Irish fest and Festa Italiana to Summerfest.