Everything you need to know about Lollapalooza 2021

Chicago’s biggest music festival returned over the weekend. Here’s all of the Sun-Times’ coverage from Grant Park in one place.

SHARE Everything you need to know about Lollapalooza 2021
Fans gather to watch Neal Francis perform on day four of Lollapalooza in Grant Park.

Fans gather to watch Neal Francis perform on day four of Lollapalooza in Grant Park, Sunday, Aug. 1, 2021.

Anthony Vazquez/Sun-Times

Lollapalooza officially returned to Grant Park this week for four days of music and good times despite concerns about how bringing together over 100,000 people each day will affect the ongoing pandemic.

The festival, which opened Thursday with vaccination or proof of a negative COVID-19 test required for entry, represented the largest public event to date held in Chicago since the emergence of the coronavirus last March. Despite worries over the virus’ Delta variant and rising caseloads nationally, the show went on over the weekend.

Late Friday, the festival announced that masks would be required in any indoor space throughout the Grant Park grounds beginning Saturday. Attendees would be encouraged to bring their own masks.

Huge acts lured giant crowds to the park, including Miley Cyrus, Foo Fighters, Post Malone and Tyler, The Creator.

The Sun-Times was there all four days covering the big shows and big crowds. Here’s what we saw.

Photo highlights

DAY 4 highlights: sights from Sunday

Dee Radke of Radkey performs on day four of Lollapalooza.

Dee Radke of Radkey performs on day four of Lollapalooza in Grant Park, Sunday, Aug. 1, 2021.

Anthony Vazquez/Sun-Times

Check out more sights and sounds captured by our photographers on the fourth day of Lolla here.

DAY 3 highlights: sights from Saturday


Festival-goers cheer as Michigander performs on day three of Lollapalooza in Grant Park on Saturday.

Ashlee Rezin/Sun-Times

Check out more sights and sounds captured by our photographers on the third day of Lolla here.

DAY 2 highlights: Sights from Friday


Tobi Lou performs on Day 2 of Lollapalooza 2021.

Pat Nabong/Sun-Times

Check out more sights and sounds captured by our photographers on the second day of Lolla here.

DAY 1 highlights: Sights from Thursday


Miley Cyrus performs at the T-Mobile stage, Thursday, July 29, 2021.

Tyler LaRiviere/Sun-Times

Black Pumas performs at the T-Mobile stage, Thursday.

Black Pumas performs at the T-Mobile stage, Thursday.

Tyler LaRiviere/Sun-Times

Check out more sights and sounds captured by our photographers on the first day of Lolla here.

Set reviews

DAY 4: Radkey, Neal Francis

There was no rest on Sunday as Lollapalooza ushered in a day of pure rock with brothers in punk music (and real life) Radkey opening things up on the Grubhub Stage.

Based on their explosive sound, catchy hooks and gritty vocals, you’d expect these three to have been around a few blocks and hailed from one of the two rock meccas: Detroit or New York City. But they’re barely out of their teens. And from Missouri.

The flannel-and-denim-clad brothers paid a nod to their ages with the bombastic “Rock & Roll Homeschool,” a tongue-in-cheek nod to The Ramones, of course. And that’s just one of their well-educated influences. Guitarist and vocalist Dee Radke (whose name clearly paved the way for destiny) is a dead ringer in vocal style for Glenn Danzig and there’s a bit of The Stooges percolating in their songwriting too.

Read all of Selena Fragassi’s reviews from Sunday here.

DAY 3: Cannons, Michigander

Michigander’s Jason Singer swore he thought he’d only see about 20 people at his set, but there was easily 100x that amount of revelers taking in the easy-like-Saturday-afternoon performance delivering perfectly crafted indie pop.

Of course hailing from Michigan (Detroit, to be specific), Singer and crew imbued that laidback Midwest attitude in both their music and their exultation for being tapped for a spot at Lollapalooza.

The frontman commented several times it was a “dream come true” and something he could only pine for as a high schooler when he first began writing music like the song “Fears.” But with his talent, it was really only a matter of time until people started listening – and they have.

Read all of Selena Fragassi’s reviews from Saturday here.

DAY 2: Tyler the Creator, Mick Jenkins, Polo G, Omar Apollo

Tyler, the Creator was trending on social media ahead of his headlining set to close out Day 2 of Lollapalooza. Half of the people were upset the festival was not yet streaming his performance on Hulu and had chosen to broadcast Marshmello instead, and the other half were pleading with the universe to make his rumored appearance with his Odd Future cohort Frank Ocean happen (though that seemed like a tall order).

One was righted as the livestream picked up the performance a half-hour later, thankfully allowing a much larger crowd to pay witness to the visionary, art-driven set that melded jazz, R&B, rap, trip hop, and darkcore.

The Grammy Award winner astutely merged the worlds of live theater and concert in his hour-plus set, sparing no effort to bring his full production stage the “creator” part of him is known for, even as live touring just starts to make its comeback and while most sets this weekend have been understandably scaled back. 

Read all of Selena Fragassi’s and Matt Moore’s reviews from Friday here.

DAY 1: Miley Cyrus, Black Pumas, Orville Peck, Playboi Carti, Jimmy Eat World

Starting her Lollapalooza headlining set with “We Can’t Stop” (preaching the general theme of “it’s my party and I’ll do what I want to”), Miley Cyrus set the tone early on: It would be one helluva time and she would be making all the rules. In following those two tenets, the genre-bending star dominated the festival’s opening night.

There were fireworks, some memorable covers, a motley crew of guests, moments of nearly flashing the videofeed cameras, and the artist taking a stand on the important of freeing Britney Spears. During Cyrus’ performance Thursday of her hit “SMS (Bangerz),” which features Spears, the jumbo screens next to the stage broadcast the trending #freebritney message superimposed with caricatures of handcuffs. (Cyrus recently championed Spears’ conservatorship emancipation at a show in Vegas too.)

Read all of Selena Fragassi’s and Matt Moore’s reviews from Thursday here.

DaBaby’s performance canceled amid backlash over homophobic comments

Rapper DaBaby was pulled from Sunday’s Lollapalooza amid a brewing controversy over homophobic comments he made during another festival performance last week in Florida.

DaBaby, real name Jonathan Kirk, has come under heavy fire after he went on a controversial rant last Sunday at the Rolling Loud music festival in Miami Gardens, Florida, that targeted gay people and those living with sexually transmitted diseases.

Read the full story here.

Lightfoot takes the stage: ‘Thank you for masking up and vaxing up’

Mayor Lori Lightfoot, who has been outspoken about her decision to keep Lollapalooza as scheduled despite the uptick in cases of COVID-19 and numerous variants spreading around the country, made a not-so-surprise appearance on the festival’s opening day.

Wearing a Black Pumas T-shirt, she introduced the group’s midday set at the T-Mobile Stage and hailed the Pumas as one of the greatest rock bands of today.

“The rate of vaccination in this crowd is off the charts,” she said.

Read the full story here.

First Lolla fans optimistic as 2021 festival kicks off amid COVID-19 precautions

Thousands of fans streamed into Grant Park Thursday marking the return of Lollapalooza after COVID-19 halted last year’s iteration of the 30-year-old music festival. While some fans said they were slightly worried about COVID-19, many expressed confidence in Lollapalooza’s new protocols.

But not everyone knew about the vaccine mandate in order to attend the music festival.

Read the full story here.

Lolla signs warn attendees they assume risk for COVID-19

The thousands of people entering Lollapalooza on Thursday are being greeted by signs explaining something that’s not included on their public health and safety website: By attending the festival, “you voluntarily assume all risks related to exposure to COVID-19,” which they mention “can lead to severe illness and death.”

Read the full story here.

Must-see acts to check out

Some of the names on the Lolla lineup are a lot bigger than others. Selena Fragassi parses through the dozens of bands and artists to break down 10 must-see acts that attendees won’t want to miss this weekend. Here’s what Fragassi says about one of the festival’s earliest performers, Orville Peck:

No one exactly knows who this incognito Canadian country singer is (his trademark look is a long, fringed mask and cowboy hat) but the boudoir-looking John Wayne has heaped tons of due praise in his few years on the scene. Both for crafting a highly contagious psychedelic outlaw sound that refreshes the genre and for being an LGBTQ iconoclast whose work with Trixie Mattel and Gaga will soon put him in a new league.

Check out all of our recommended shows here.

How to watch performances live online

Unlike past years, Hulu is the exclusive live streaming partner for Lollapalooza 2021. All Hulu subscribers will be able to watch live performances for free as part of their subscriptions. Complete streaming schedules for all four days are already up on Hulu’s website, although they warn that set times are subject to change.

How will COVID-19 affect the festival?

With coronavirus case figures rising across the country amid lagging vaccination rates and the emergence of the Delta variant, Lollapalooza put in place security measures to help make the festival safer.

For those attending the festival, a vaccination card or proof of negative COVID-19 test will be required for entry. Get more information on how that’ll work here.

Chicago’s top health official, Dr. Alison Arwady, said Tuesday that the city’s virus situation is in “good control” ahead of the festival. However, Mayor Lori Lightfoot said recently that she would not hesitate to impose measures in Chicago such as face covering requirements if the city’s daily caseload keeps rising — and Arwady said she expects “some cases” of COVID-19 to result from the festival being held.

Lineup and schedule

Complete daily schedules for Thursday, Friday, Saturday and Sunday can be found here.


The after-show lineup includes Modest Mouse, Journey, Jimmy Eat World and Freddie Gibbs. Check out the complete list of official Lolla after-shows here.

The Latest
Our heroine (Hilary Swank) goes from playing hard to working hard to save an ailing girl.
An 18-year-old man was shot and hospitalized in critical condition about 5:30 p.m. Tuesday in the 4800 block of South Marshfield Avenue . A 40-year-old man was taken into custody after a 40-minute standoff.
Despite trailing for much of the game, the Roadrunners were prepared for these close battles thanks to their.trip to Florida for the Tampa Bay Christmas Invite.
Definition Theatre and Timeline Theatre Company were each awarded $180,000; Chicago Children’s Theatre received $100,000 and Remy Bumppo Theatre Company $50,000.