Festivals Chicago 2019

The juggernaut music festival takes over one mile of Grant Park and draws 400,000 attendees over the course of four days. The 2019 event featured some 170 acts—including Ariana Grande and Childish Gambino—on eight stages. Sponsor activations were also robust, with brands such as Red Bull and American Eagle setting up elaborate activations on festival grounds. The event is said to generate $5 million for the City of Chicago each year. Next: July 30-August 2, 2020

See more: Lollapalooza 2019: Inside Guest-Focused Brand Activations from Brands Like Pepsi and Cupcake Winery

The brainchild of Pitchfork magazine, this festival in Chicago’s Union Park draws around 50,000 guests each year. In 2019, headliners included Haim, Robyn, and Belle & Sebastian. Festival grounds also held sponsor activations from brands such as Kind snacks and Svedka vodka. A distinguishing feature of Pitchfork is its low ticket prices: guests may purchase a day pass for $75. Next: Summer 2020

With the theme Lights, Camera, Napkin, the 2019 festival drew around 14,000 foodies. More than 100 chefs, including Michael Mina, Rick Bayless, and Andrew Zimmern, appeared at the prestigious food fest. Held on Millennium Park’s Great Lawn, the event featured gourmet food tastings at tented pavilions, wine samples, seminars, and food demos. In keeping with the year’s theme, the demos took on cinematic title such as “Eat, Plate, Love.” Next: September 25-27, 2020

Billed as the largest free show of its kind in the United States, this summertime tradition sees daring stunts from the U.S. Navy Blue Angels, the U.S. Army Parachute Team Golden Knights, and more. Each year, some 2 million spectators take in the deafening show. Next: August 15-16, 2020

Billed as the largest free outdoor food festival in the world, this year’s event offered snacks from 82 participating restaurants. Besides bites ranging from turkey legs to vegan tamales and kimchi cheese fries, the festival featured art, dance performances, and free concerts from acts such as India.Arie. More than one million guests attended. Next: Summer 2020

Up from #7
Celebrating its 15th anniversary in 2019, this multi-day festival showcases a range of musical genres including punk, metal, alternative, and hip-hop. Held once again in Douglas Park, the event featured internationally known acts such as Blink-182, Wu Tang Clan, and Bikini Kill on five stages. As usual, there were also carnival games and sideshow performances including a butter sculptor. The event typically draws some 40,000 guests per day. Next: Summer 2020

Up from #10
Now in its 81st year, this 10-week festival highlights classical music with concerts in Millennium Park. In 2019, the long-running fest introduced a series of programs called Festival Next. Aimed at reimagining the concert-going experience, the initiative included free concerts on Sunday afternoons, as well as a multimedia experience with the Grant Park Orchestra. Next: Summer 2020

Up from #11
Billed as the largest street festival in the Midwest, Market Days draws an estimated 100,000 guests each year. Covering a half a mile of Chicago’s “Boystown” neighborhood in Lakeview, the event features more than 250 vendors, food and drink, dancing and DJs, and live music on five stages. This year, performers included Sheila E. and Icona Pop. Next: August 8-9, 2020

Some 30,000 attendees turn out to this annual festival, which features more than 250 speakers. The week also offers 200-plus events, which range from onstage talks to intimate labs that take guests behind the scenes at Chicago businesses. This year, those businesses included a film studio as well as a spot that offers yoga with adoptable bunnies. Speakers include Jill Biden and fitness expert Hannah Bronfman. Next: October 12-17, 2019

Now in its 36th year, this free event is considered the largest blues festival in the world. In 2019, headliners included Bobby Rush and the Kinsey Report. The entertainment takes place on six stages in Millennium Park, and the fest typically draws some 50,000 music fans. Next: June 5-7, 2020

This internationally broadcast fest has been running in Chicago for 41 years. The event features performances from Chicago-based jazz artists, as well as international performers. Free-admission concerts are held throughout the city, including in iconic landmarks such as Millennium Park and the Chicago Cultural Center. Next: Summer 2020

Celebrating ribs and rock and roll for 21 years, this lively street fest is famous for serving 50,000 pounds of meat throughout its three-day run. In addition to meaty eats from some 30 vendors, the event dishes out 25 hours of diverse music programming. There’s also family entertainment and “Best Ribs” contests. Next: Summer 2020

Held in a section of Chicago that once housed multiple printing presses, this free book fair and literary festival drew 125,000 attendees in 2019. New features of this year’s event included an Arts & Poetry tent and a storybook-theme parade for children; the fest also showcased books from some 100 booksellers. Next: June 6-7, 2020

Lincoln Square’s summer bash celebrates suds and songs. The event serves up neighborhood fare paired with more than 40 regional craft beers; its four stages host performances from some 70 bands. There are also market vendors slinging jewelry, natural beauty products, and more. More than 30,000 attendees turn out each year. Next: Summer 2020

Held in Grant Park’s Spirit of Music Garden, this free event offers alfresco dance classes followed by live music from nearly 50 different bands and DJs. Dance and music styles range from swing to waltz and cha-cha throughout the summer. Next: Summer 2020