10. Ravinia, Chicago
Every year, Chicagoans flock to this North Shore green space and spread out blankets for a concert series that stretches all summer long. You can't beat the location – "smack dab in the middle of some of the highest per-cap-income earners on the planet," in the words of Andy Cirzan, vice president of concerts for Chicago's Jam Productions. Over the years, it's welcomed a wide range of big-name acts including Bob Dylan, Rufus Wainwright, Crosby, Stills and Nash, Joni Mitchell, the Beach Boys and many more.
Fun Fact: Janis Joplin's summer 1970 Ravinia performance drew a security force of 200 police officers due to paranoia after fans rioted before a Sly and the Family Stone concert in Chicago the previous month.