8. Lollapalooza (Early August)
Chicago, Illinois
Almost all of the so-called "large footprint" destination music festivals owe a debt to Lollapalooza founder Perry Farrell, the charismatic frontman of the recently reformed Jane's Addiction. From 1991–1997, Farrell's own Lollapalooza functioned as a touring festival, and in 2005 it was reborn as a once-a-year, three-day party in Chicago's Grant Park (the festival helps raise money for open space in the Windy City). The Lollapalooza lineup continues to blaze brave new trails, showcasing up-and-coming talent, and also offers a hard-rocking change of pace from muddy jam jubilees in the middle of nowhere. Headliners such as Pearl Jam, Nine Inch Nails, and Jane's Addiction—who got their start when grunge was still young—continue to storm the Lollapalooza stage, while R&B and hip-hop acts such as the Beastie Boys, Gnarls Barkley, and Kanye West have made appearances. Dance the night away at Perry's, where world-class DJs will spin, or kick back with cold craft beers at Lederhosen's Biergarten. Additionally, parents who want to start the music education young will be interested to know about Kidzapalooza, a popular family-friendly interactive area in Grant Park. Kids under ten can listen to music for free, provided they are in the company of a ticket-holding grownup, and can be rock stars for the day with temporary tattoos and punk hairstyles, and play instruments in the Jam Tent with a full band set up.

Hot tip: If the downtown hotels threaten to blow your budget, Lollapalooza's organizers suggest taking advantage of Roomorama.com, an online peer-to-peer rental service.

Chicago Travel Guide