1. Lollapalooza
#1 Festival
Chicago’s largest music festival returned this year to Grant Park with 180 acts on eight stages, welcoming about 100,000 revelers a day. Headliners included The Weeknd, Bruno Mars, Arctic Monkeys, and Jack White. For 2018, sponsor Toyota brought in stylists for festival-ready hair and attendees could even order pizza between sets via the Lolla app. Next: August 1-4, 2019
Chicago’s largest music festival returned this year to Grant Park with 180 acts on eight stages, welcoming about 100,000 revelers a day. Headliners included The Weeknd, Bruno Mars, Arctic Monkeys, and Jack White. For 2018, sponsor Toyota brought in stylists for festival-ready hair and attendees could even order pizza between sets via the Lolla app. Next: August 1-4, 2019
Photo:Â Barry Brecheisen/BizBash
2. Pitchfork Music Festival
#2 Festival
This year’s fest showcased more than 40 bands with headliners including Tame Impala, Fleet Foxes, and Lauryn Hill, who presented a special 20th-anniversary performance. Some 60,000 people came to the fest at Chicago’s Union Park. In 2018, a new partnership with RAINN helped raise awareness on sexual violence. A portion of the proceeds went toward the foundation, including sales from sponsor Goose Island, which created a beer specifically for the event. Next: Summer 2019
This year’s fest showcased more than 40 bands with headliners including Tame Impala, Fleet Foxes, and Lauryn Hill, who presented a special 20th-anniversary performance. Some 60,000 people came to the fest at Chicago’s Union Park. In 2018, a new partnership with RAINN helped raise awareness on sexual violence. A portion of the proceeds went toward the foundation, including sales from sponsor Goose Island, which created a beer specifically for the event. Next: Summer 2019
Photo:Â Pooneh Ghana
3. Chicago Gourmet
#3 Festival
Presented by Bon Appétit, the 2018 edition celebrated a new theme, Rock the Fork, for the 11th annual event in Millennium Park. This year, chef headliners included Stephanie Izard, Graham Elliot, and Rick Bayless. Guests were entertained by unique culinary experiences from the Italian Feast on the Symphony Center stage to the popular Hamburger Hop, as well as live demos and restaurant samplings. Next: Fall 2019
Presented by Bon Appétit, the 2018 edition celebrated a new theme, Rock the Fork, for the 11th annual event in Millennium Park. This year, chef headliners included Stephanie Izard, Graham Elliot, and Rick Bayless. Guests were entertained by unique culinary experiences from the Italian Feast on the Symphony Center stage to the popular Hamburger Hop, as well as live demos and restaurant samplings. Next: Fall 2019
Photo:Â Bonnie Rezabek
4. Chicago Air and Water Show
#4 Festival (up from #5)
Sprawling crowds packed the lakeshore to see aerobatics and simulated water rescues at the largest free event of its kind. For 2018, fans watched the 60th anniversary of awe-inspiring stunts, which included the U.S. Air Force Thunderbirds, U.S. Navy Parachute Team Leap Frogs, and the U.S. Army Parachute Team Golden Knights, who brought along Chicago rapper Che “Rhymefest” Smith for a tandem jump. Next: August 2019
Sprawling crowds packed the lakeshore to see aerobatics and simulated water rescues at the largest free event of its kind. For 2018, fans watched the 60th anniversary of awe-inspiring stunts, which included the U.S. Air Force Thunderbirds, U.S. Navy Parachute Team Leap Frogs, and the U.S. Army Parachute Team Golden Knights, who brought along Chicago rapper Che “Rhymefest” Smith for a tandem jump. Next: August 2019
Photo:Â Ron Sellers
5. Taste of Chicago
#5 Festival
Every summer since 1980, Grant Park transforms into the world’s largest food festival. Approximately 1.5 million people visited the fest that shows off 70 of Chicago’s unique culinary eateries. This year, major musical acts were showcased including Brandi Carlile, The Flaming Lips, and George Clinton Parliament Funkadelic. Next: Summer 2019
Every summer since 1980, Grant Park transforms into the world’s largest food festival. Approximately 1.5 million people visited the fest that shows off 70 of Chicago’s unique culinary eateries. This year, major musical acts were showcased including Brandi Carlile, The Flaming Lips, and George Clinton Parliament Funkadelic. Next: Summer 2019
Photo: Courtesy of Taste of Chicago
6. Chicago Ideas Week
#6 Festival (up from #9)
Known as the largest ideas festival, the event typically draws some 30,000 attendees. This year features a variety of speakers including actress Ellie Kemper, March For Our Lives co-founder David Hogg, and former New Orleans Mayor Mitch Landrieu. Next: Fall 2019
Known as the largest ideas festival, the event typically draws some 30,000 attendees. This year features a variety of speakers including actress Ellie Kemper, March For Our Lives co-founder David Hogg, and former New Orleans Mayor Mitch Landrieu. Next: Fall 2019
Photo:Â Lois Bernstein/Chicago Ideas Week
7. Riot Fest
#7 Festival
This year’s fest known for rock, metal, and punk was held in Chicago’s Douglas Park. Major changes to the lineup were made before the event as Blink 182 dropped out for medical reasons. Fill-ins were quick with headliners Weezer and Run the Jewels, and the show went on without a hitch. Next: September 13-15, 2019
This year’s fest known for rock, metal, and punk was held in Chicago’s Douglas Park. Major changes to the lineup were made before the event as Blink 182 dropped out for medical reasons. Fill-ins were quick with headliners Weezer and Run the Jewels, and the show went on without a hitch. Next: September 13-15, 2019
Photo: Courtesy of Riot Fest
8. Chicago Blues Festival
#8 Festival
The first night of the festival kicked off with the 65th Anniversary of Delmark Records Celebration at Jay Pritzker Pavilion. The festival, now in its 35th year, saw headline performances including a special tribute to Bob Koester, Willie Clayton, and Mavis Staples. Next: Spring 2019
The first night of the festival kicked off with the 65th Anniversary of Delmark Records Celebration at Jay Pritzker Pavilion. The festival, now in its 35th year, saw headline performances including a special tribute to Bob Koester, Willie Clayton, and Mavis Staples. Next: Spring 2019
Photo:Â Patrick L. Pyszka
9. Chicago Jazz Festival
#9 Festival
Chicago’s jazz fest celebrated its 40th year over Labor Day Weekend. Headliners at Millennium Park included Ramsey Lewis and Orbert Davis' Chicago Jazz Philharmonic. In 2018, the event also featured youth groups Roof Top Jazz: Young Jazz Lions, and NextGenJazz. Next: Summer 2019
Chicago’s jazz fest celebrated its 40th year over Labor Day Weekend. Headliners at Millennium Park included Ramsey Lewis and Orbert Davis' Chicago Jazz Philharmonic. In 2018, the event also featured youth groups Roof Top Jazz: Young Jazz Lions, and NextGenJazz. Next: Summer 2019
Photo: Courtesy of Chicago Jazz Festival
10. Grant Park Music Festival
#10 Festival
The festival has been a Chicago tradition of classical music for more than 80 years. For 2018, the free, 10-week season featured classical music performed by the Grant Park Orchestra and Chorus. Highlights included the Young Artist Showcase, a pre-concert lecture series, and rehearsals open to the public. Next: Summer 2019
The festival has been a Chicago tradition of classical music for more than 80 years. For 2018, the free, 10-week season featured classical music performed by the Grant Park Orchestra and Chorus. Highlights included the Young Artist Showcase, a pre-concert lecture series, and rehearsals open to the public. Next: Summer 2019
Photo: Norman-Timonera
11. Northalsted Market Days
#11 Festival
More than 300,000 people typically attend this massive two-day street festival in Boystown. This year, guests enjoyed several photo opportunities including an Enjoy Illinois temporary art installation dubbed “Amazing for All.” The diverse schedule also showcased international DJs and headliners, including Betty Who and MAX. Next: August 10-11, 2019
More than 300,000 people typically attend this massive two-day street festival in Boystown. This year, guests enjoyed several photo opportunities including an Enjoy Illinois temporary art installation dubbed “Amazing for All.” The diverse schedule also showcased international DJs and headliners, including Betty Who and MAX. Next: August 10-11, 2019
Photo:Â Steven Koch
12. Ribfest Chicago
#12 Festival (up from #13)
The fest, hosted by the Northcenter Chamber of Commerce, turned 20 this year. More than 32,000 people came out to indulge in 50,000 pounds of barbecue and take in 25 hours of music including honky tonk, indie, and rock. Organizers added a Kids Square in 2018 that was full of fun family activities. Next: June 7-9, 2019
The fest, hosted by the Northcenter Chamber of Commerce, turned 20 this year. More than 32,000 people came out to indulge in 50,000 pounds of barbecue and take in 25 hours of music including honky tonk, indie, and rock. Organizers added a Kids Square in 2018 that was full of fun family activities. Next: June 7-9, 2019
Photo:Â Steven E Gross
13. Printers Row Lit Fest
#13 Festival
The fair was founded in 1985 to get more traction in Printers Row—then the city’s bookmaking hub. Fast forward and it’s now the Midwest’s largest literary festival. The fest brings in some 150,000 book lovers in two days. Headliners included author Joyce Carol Oates, Cubs World Series champion David Ross, and chef Paul Kahan. Next: June 2019
The fair was founded in 1985 to get more traction in Printers Row—then the city’s bookmaking hub. Fast forward and it’s now the Midwest’s largest literary festival. The fest brings in some 150,000 book lovers in two days. Headliners included author Joyce Carol Oates, Cubs World Series champion David Ross, and chef Paul Kahan. Next: June 2019
Photo:Â Barry Brecheisen
14. Square Roots Festival
#14 Festival (new to the list)
Since 2012, this Lincoln Square festival features musical entertainment, a variety of food, regional craft beer, and a bustling market of unique vendors. In 2018, 70 global bands performed on four stages. A Highlight this year included a partnership with the European Union that featured “Getting to Know Europe” artists. The event supports Lincoln Square Ravenswood Chamber of Commerce and Old Town School of Folk Music’s programming. Next: July 12-14, 2019
Since 2012, this Lincoln Square festival features musical entertainment, a variety of food, regional craft beer, and a bustling market of unique vendors. In 2018, 70 global bands performed on four stages. A Highlight this year included a partnership with the European Union that featured “Getting to Know Europe” artists. The event supports Lincoln Square Ravenswood Chamber of Commerce and Old Town School of Folk Music’s programming. Next: July 12-14, 2019
Photo: Courtesy of Square Roots Festival
15. Chicago Summerdance
#15 Festival
The annual outdoor live music and dancing series is the largest of its kind in the United States. Held in Grant Park’s Spirit of the Music Garden, the free, outdoor classes featured a lineup of nearly 50 different live bands and DJs. In 2018, those who attended Taste of Chicago could also enjoy these events in the evening. Next: Summer 2019
The annual outdoor live music and dancing series is the largest of its kind in the United States. Held in Grant Park’s Spirit of the Music Garden, the free, outdoor classes featured a lineup of nearly 50 different live bands and DJs. In 2018, those who attended Taste of Chicago could also enjoy these events in the evening. Next: Summer 2019
Photo:Â Patrick L. Pyszka/City of Chicago
