If you're into music or any outdoor performance, you've got to attend something, anything, in Millenium Park at the Jay Pritzker Pavillion. Spread out a blanket with someone special on the 95,000-square-foot lawn (it seats 7,000 so don't expect privacy), which is often free. If you want a traditional seat, 4,000 fixed seats are available for a fee based on the performance. Frank Gehry designed it so if you're a fan, you'll appreciate the structure itself; a canopy of crisscrossing steel pipes and a steel "headdress" suspend 100 speakers to frame the proscenium stage. Home of the infamous "bean" sculpture - you know, the sculpture where everyone takes a photo of their own reflection? the Jay Pritzker pavilion hosts live classical, pop, rock, and even film nights in spring and summer, attracting hundreds of Chicagoans and visitors who descend with picnic baskets and bottles of wine in hand.

jaypritzkerpavilion.com