1. Lollapalooza

#1 Festival
After drawing 90,000 music fans a day—its largest crowd to date—to Grant Park in 2011, Lollapalooza returned to the urban park this past weekend. Among the 130 acts on the line up were the Red Hot Chili Peppers and Florence & the Machine. Next: August 2-4, 2013
After drawing 90,000 music fans a day—its largest crowd to date—to Grant Park in 2011, Lollapalooza returned to the urban park this past weekend. Among the 130 acts on the line up were the Red Hot Chili Peppers and Florence & the Machine. Next: August 2-4, 2013
Photo: Courtesy of Lollapalooza
2. Chicago Air and Water Show

#3 Festival
The iconic local tradition—scored with the sounds of thrillingly loud engines—lures two million spectators to the lakefront. In the corporate hospitality area of the Chicago Air and Water Show, companies such as Shell and Boeing host parties. Next: August 18-19, 2012
The iconic local tradition—scored with the sounds of thrillingly loud engines—lures two million spectators to the lakefront. In the corporate hospitality area of the Chicago Air and Water Show, companies such as Shell and Boeing host parties. Next: August 18-19, 2012
Photo: Courtesy of City of Chicago
3. Chicago Blues Festival

#4 Festival (up from #5)
Chicago puts on the world’s largest free blues festival, which this year was headlined by Mavis Staples and drew 500,000 fans. Next: June 2013
Chicago puts on the world’s largest free blues festival, which this year was headlined by Mavis Staples and drew 500,000 fans. Next: June 2013
Photo: Courtesy of City of Chicago
4. Chicago Jazz Festival

#5 Festival (up from #6)
A Labor Day weekend tradition, the Chicago Jazz Festival has four stages with free performances from big-name artists such as Diane Reeves. Next: August 30-September 2, 2012
A Labor Day weekend tradition, the Chicago Jazz Festival has four stages with free performances from big-name artists such as Diane Reeves. Next: August 30-September 2, 2012
Photo: Courtesy of City of Chicago
5. Chicago Gourmet

#6 Festival (up from #9)
Though a relative newbie to the festival scene, Chicago Gourmet has quickly built a reputation the city’s most prestigious food and wine event, and now attracts crowds of 10,000-plus. (In 2008, its first year, the festival drew 6,000 guests.) Showcasing 100 high-end restaurants and hundreds of international vintners, breweries, and spirit makers, the gathering also offers celebrity chef cooking demos, book signings, and popular events such as the "Hamburger Hop." Next: September 28-30, 2012
Though a relative newbie to the festival scene, Chicago Gourmet has quickly built a reputation the city’s most prestigious food and wine event, and now attracts crowds of 10,000-plus. (In 2008, its first year, the festival drew 6,000 guests.) Showcasing 100 high-end restaurants and hundreds of international vintners, breweries, and spirit makers, the gathering also offers celebrity chef cooking demos, book signings, and popular events such as the "Hamburger Hop." Next: September 28-30, 2012
Photo: Courtesy of Chicago Gourmet
6. Taste of Chicago

#7 Festival
Chicago’s sprawling food festival, once the city’s most successful large-scale event, has been revamped to address declining attendance and profits in recent years. This year, the Illinois Restaurant Association managed Taste of Chicago, shortening it from 10 to five days, adding attractions such as pop-up restaurants, and inviting guests to purchase tickets to concerts by Jennifer Hudson. Some one million guests attended and many vendors reported increased profits. Next: July 2013
Chicago’s sprawling food festival, once the city’s most successful large-scale event, has been revamped to address declining attendance and profits in recent years. This year, the Illinois Restaurant Association managed Taste of Chicago, shortening it from 10 to five days, adding attractions such as pop-up restaurants, and inviting guests to purchase tickets to concerts by Jennifer Hudson. Some one million guests attended and many vendors reported increased profits. Next: July 2013
Photo: Courtesy of City of Chicago
7. Grant Park Music Festival

#8 Festival
The free, outdoor classical music festival celebrates its 50th anniversary this year, with a number of events that included a first-of-its-kind simulcast of the Paris Opera Ballet’s performance of Giselle from the Harris Theater on June 27. Next: June 13-August 18, 2012
The free, outdoor classical music festival celebrates its 50th anniversary this year, with a number of events that included a first-of-its-kind simulcast of the Paris Opera Ballet’s performance of Giselle from the Harris Theater on June 27. Next: June 13-August 18, 2012
Photo: Norman Timonera/Courtesy of Grant Park Music Festival
8. Chicago SummerDance

#10 Festival
Regarded as one of the largest outdoor dance-class series in the United States, Chicago SummerDance teaches an average of 1,200 participants per session. Participants get free classes in everything from swing to polka, then test their moves on an open-air dance floor with a live band. Next: July 19-September 16, 2012
Regarded as one of the largest outdoor dance-class series in the United States, Chicago SummerDance teaches an average of 1,200 participants per session. Participants get free classes in everything from swing to polka, then test their moves on an open-air dance floor with a live band. Next: July 19-September 16, 2012
Photo: Courtesy of City of Chicago/Department of Cultural Affairs and Special Event
9. Printers Row Lit Fest

#12 Festival
The Midwest’s largest free, outdoor literary event fills five city blocks with wares from some 200 booksellers and also has a poetry slam and book signings. This year, writers such as Sapphire and poet Mark Doty made appearances at the Printers Row Lit Fest. Next: June 2013
The Midwest’s largest free, outdoor literary event fills five city blocks with wares from some 200 booksellers and also has a poetry slam and book signings. This year, writers such as Sapphire and poet Mark Doty made appearances at the Printers Row Lit Fest. Next: June 2013
Photo: Glenn Kaupert Photography