Come in June/July!!! Best weather (not too hot) and lots of festivals (Blues fest, taste of Chicago, concerts-all free in Grand park) and neighborhood festivals. If you want to go to the beach, try North beach for lots of Volleyball and specially on weekend lots of people. If you'd like it a little more quiet, go to Oak beach at the end of the shopping part of Michigan Ave. (north) For bars, restaurants and cafes go to Old town and Wriggleyville. And of course check out Wrigley Field, the 2nd oldest baseball stadium of the world (after Boston). The games there are known for the best atmosphere!!!! Go Cubbies!!!!!!!