#1 Festival
Spanning four days, this year’s sold-out music fest offered performances from 170 acts, including Chicago native Chance the Rapper. Some 100,000 music fans attended the Grant Park event each day, and sponsors such as Toyota and Red Bull hosted activations on festival grounds. Next: August 2-5, 2018
#2 Festival
In 2017, the indie music festival offered a lineup featuring more than 40 acts. Solange, PJ Harvey, and Angel Olsen were among the artists who played for a crowd of some 50,000 total guests. There were also on-site specialty fairs, along with activations from OKCupid, Wendy’s, and other brands. Next: Summer 2018
#3 Festival
In 2017, the prestigious food festival celebrated its 10th anniversary. Held in Millennium Park, the event is presented by Bon Appetit. Headliners this year included chefs Carla Hall, Curtis Stone, and Rick Bayless; there were also cocktail seminars, book signings, and restaurant tastings. New this year was a weeklong celebration called Extraordinary Chefs—Extraordinary Places, which featured 10 chef-hosted dinner parties in iconic Chicago locations. Next: Fall 2018
#4 Festival
In its 37th year, the food festival offered snacks from some 60 vendors. Other highlights included two stages for live music, five chef-planned dinners, and 35 cooking demos. There was also a new arts area that featured performances and works from local artists. Organizers estimated that attendance was 1.6 million guests, which marked the largest crowd since 2012. Next: Summer 2018
#5 Festival
Chicago’s Air and Water Show is billed as the largest free event of its kind in the United States. Some two million fans take in the show, which features high-flying stunts from military and civilian teams. This year, highlights included stunts from the U.S. Navy Blue Angels and U.S. Army Parachute Team Golden Angels. Next: August 2018
#6 Festival
Held in Chicago’s Douglas Park, the rock, metal, and punk music festival features performances on five main stages. This year, headliners included Nine Inch Nails, New Order, and Ministry. Other attractions on festival grounds include circus acts and carnival games. Next: September 14-16, 2018
#7 Festival
Billed as the world’s largest free blues festival, the musical event is now in its 34th year. The 2017 lineup featured a more diverse array of performers than in past years, and included rapper Rhymefest and roots singer Rhiannon Giddens. Next: Spring 2018
#8 Festival
A local tradition since 1979, the jazz festival takes place over Labor Day Weekend. In 2017, the event offered performances from local jazz artists, along with national and international talent. Headliners this year included Jason Moran and the Dave Rempis Quintet. Summer 2018
#9 Festival
Composed of talks, panel discussions, and hands-on experiences, the event is described as a “think festival.” In 2017, high-profile speakers included cosmetics guru Bobbi Brown, fashion designer Zac Posen, and Teen Vogue’s buzzy editor Elaine Welteroth. The event draws some 30,000 attendees. Next: Fall 2018
#11 Festival
Billed as the Midwest’s largest street festival, the two-day event draws more than 300,000 people. Held in Chicago’s Boystown neighborhood, the festival is now in its 36th year. In 2017, it featured performances from 40 acts, including singer Tiffany. There were also some 300 arts, crafts, and food vendors. Next: August 2018
#12 Festival
The 33-year-old festival spans five city blocks, and typically draws some 150,000 book-lovers. The event also features tomes from 200 booksellers, and appearances from 200 authors. This year, visiting authors included U.S. Senator Al Franken and Dani Shapiro. Next: Spring 2018
#13 Festival (new to the list)
Held along Lincoln Avenue, the meaty event has been featured on the Food Network and in USA Today. The festival, which draws around 40,00 guests, offers snacks from 13 rib restaurants, but there are also vendors slinging everything from fried green tomatoes to Hawaiian pork tacos. Other highlights include live bands on two stages and activities for kids. Next: June 8-10, 2018
#14 Festival
Held in Grant Park’s Spirit of the Music Garden, the event offers free, open-air dance classes throughout the summer, as well as live music. This year, the lineup featured some 48 bands who played music styles ranging from swing to waltz and cha-cha. Next: Summer 2018
