- Downtown Sound: New Music Mondays, which runs from May 24 - July 26
- Music Without Borders Presents, which is every Thursday from June 3 - July 22
All of these shows will start at 6:30 PM and end at 9:00 PM, but get there early for some of the bigger names that will be coming through. In 2007, The Decemberists (accompanied by the Grant Park Orchestra) drew 11,000 - 15,000 fans. As someone standing around the periphery for that show, I assure you that getting a spot on the lawn, if not the seats, is a must.
The free music season gets off to a great start with Besnard Lakes and The Ponys playing Monday, May 24, and then The Very Best and Balkan Beat Box on Thursday, June 3. Other shows to put a star next to or highlight are She & Him and Hollows (6/7), The Books and Via Tania (6/21), and Orchestre Poly-Rythmo de Cotonou with La 33 (7/15).
Check out the full schedule of shows here. After that, grab some friends and a blanket and hit the grass.