One item that Mayor Daley deserves a lot of credit for championing to completion is Millennium Park in Chicago. Millennium Park is famous for the "Bean" (or more formally known as Cloud Gate, although no one calls it that) the giant polished, well, bean thing.
On evening nights in the summer at the Jay Pritzker Pavilion they have free concerts. The concerts cover a variety of music types but mostly focus on classical music. The pavilion has seats up front (with a few takers) but the real fun is out in the lawn. There are interlaced steel supports with speakers so that you can hear the concert even if you can't really see the stage, which is fine because not much happens at a classical music concert.
It is great to pack a picnic and sit out on the lawn. At night, the concert band shell turns colors between blue and orange and others (it looks better than it sounds, it isn't garish) and you can lay on the grass and look at all the tall buildings. It is OK to bring a bottle of wine and most people on the lawn have wine and dinner with blankets, chairs and tables. If you are coming from out of town or the suburbs, you can park in a garage right under the pavilion and walk over. Amazingly enough, they even have restrooms that are large, clean and well lit; a Soldier Field veteran like Dan or I can't believe that the city has public bathrooms that aren't completely fouled, but it is the truth.
Here is a brief movie showing the pavilion after the band is done with a view of the buildings along the park. My movie skills aren't the greatest, trust me it is even better in person.