#1 Festival
This year, the megawatt music fest celebrated its 25th anniversary and added another day to its lineup. The sold-out event—which spanned four days this year—featured performances from 170 acts, as opposed to 130 acts in 2015. Some 100,000 music fans flocked to the fest each day to hear music from the likes of the Red Hot Chili Peppers and Lana Del Rey. Next: August 3-6, 2017
#2 Festival
Now in its 11th year, Pitchfork’s celebration of independent music takes place annually in Union Park, and draws around 50,000 guests. The 2016 lineup featured 40-some acts, among them Beach House and Sufjan Stevens. As usual, the fest included craft, record, and poster fairs, along with sponsor activations from brands like Vans. Next: July 2017
#3 Festival
In 2016, the sold-out festival introduced the concept of a “host chef,” tapping the famed Rick Bayless to fill the role. For the first time, the event also had a theme: “Food is Art.” The fest featured some 250 chefs in tastings, demonstrations, and more; there were also separately ticketed events including the popular burger tasting, dubbed the “Hamburger Hop.” Total attendance was 13,694 guests. Next: September 22-24, 2017
#4 Festival
Now in its 36th year, the outdoor food festival showcases bites from 67 local restaurants. This year, some 1.4 million guests tried snacks from smoked alligator sausage to upside-down caramel cupcakes. Other features included cooking demos, celebrity chef dinners, and concerts from the likes of Billy Idol. New features included a CH Distillery cocktail lounge where guests could sip Moscow Mules and other drinks. Next: Summer 2017
#5 Festival
Known as the largest free event of its kind in the United States, the show features daredevil stunts from both military and civilian teams. Some two million fans flock to the lakefront to take in the show, which Shell has sponsored for 20 years. This year, rainy weather caused some delays, but the show carried on as usual and featured appearances from the U.S. Air Force Thunderbirds, the U.S. Army Parachute Team Golden Knights, and more. Next: August 2017
#6 Festival (up from #9)
Held in Chicago’s Douglas Park, the event that started as a punk and metal festival now features performances from some 130 bands. This year, the lineup featured the Flaming Lips, the Misfits, and Julian Marley. The event draws 160,000 attendees, and also offers a mini golf course, arcade games, and circus acts on site. This year, it was featured in The New York Times. Next: September 2017
#7 Festival
The world’s largest free blues festival draws some 500,000 fans each year. Held in Grant Park during a scorching June weekend, this year’s 33rd annual affair saw headliners on four stages. The event also featured a panel discussion on “The Great Migration”—the mass movement of African Americans from the south in 1916—and a tribute to Otis Rush. Next: Spring 2017
#8 Festival
The jazzy fest has been a local tradition since 1980. Held each year over Labor Day Weekend, the festivities include free performances from local and international artists. This year, guests took in performances from the likes of Orbert Davis and Benny Golson Quartet. Since 2016 also marked the centennial of the Great Migration, the event commemorated the anniversary with a newly commissioned work. Next: September 2017
#9 Festival
Billed as a “think festival,” the weeklong gathering features 150 events, including talks and hands-on labs. This year, speakers included Skinnygirl Cocktail founder Bethenny Frankel, film and television producer Brian Grazer, and Hollywood agent Ari Emanuel. The fest drew some 30,000 attendees. Next: October 9-15, 2017
#10 Festival
A tradition since the 1930s, the free music festival runs for 10 weeks each summer in Millennium Park. This year, highlights included a Cole Porter celebration and a movie night featuring Charlie Chaplin’s City of Lights, scored by the Grant Park Orchestra. Next: Summer 2017
#11 Festival
Known as the largest outdoor street festival in the Midwest, the event celebrated its 35th anniversary in 2016. Some 180,000 guests gathered for the fair. The event featured arts, crafts, food, and drink vendors, as well as performances from Erika Jayne and the Chicago Gay Men’s Chorus. Next: August 12, 2017
#12 Festival
Spanning five city blocks, the outdoor literary event draws around 150,000 guests. The event typically features 200 booksellers and 200 authors. This year’s fest featured appearances from the likes of former O.J. Simpson prosecutor Marcia Clark and cookbook author Dorie Greenspan. Next: June 2017
#13 Festival
Billed as the largest outdoor live music and dancing series in the United States, the event offers free dance classes in Grant Park’s Spirit of Music Garden. This year, the fest celebrated its 20th anniversary and featured 43 different bands; lessons covered swing dancing, waltzing, and more. Next: Summer 2017Â
