Whether Or Not Lollapalooza 2021 Happens, Here’s Our (Mock) Lineup Predictions

Will Lollapalooza happen this year? Will any major festival in the US happen this year? All signs point to…maybe. While lots of us remain skeptical, major production companies are treading lightly around the possibilities of festival season going off without a hitch this spring and summer, with some events into the fall. One notable festival, Life Is Beautiful, is scheduled to go on in Las Vegas this September. 3-day tickets are already sold out.

Justin Bieber is selling tickets to an arena tour, with a stop in Chicago this June. Harry Styles has rescheduled tour dates still on sale for the end of the summer and into fall. With vaccines ramping up across the United States and most recently, President Joe Biden announcing his plan to demand all states to open vaccination eligibility for all adults starting May 1, the end of this horrifying, once-in-a-lifetime pandemic is finally within reach. Only time will tell…

With that being said, here are our predictions for a POSSIBLE Lollapalooza. Though it is imaginary, since there are no current plans known to the public for this festival to happen or not happen in August 2021, anything is possible.


A$AP Rocky

Billie Eilish – does this prediction need an explanation? Billie was on the cusp of complete superstardom (if she wasn’t there already) pre-pandemic, and I’m pretty certain she would have been headlining at Lollapalooza 2020. Fresh off a couple Grammy wins and a critically-acclaimed documentary under her belt, Eilish has definitely maintained enough relevancy through COVID to still headline a festival this year (and probably next).

Disclosure – Disclosure’s 2020 release ENERGY was met with positive reviews and a Grammy nomination, plus they haven’t performed at the festival since 2016. I don’t keep up with dance music as much as I probably should, but I think Disclosure is a safe prediction to make.

Dua Lipa – Like Eilish, Dua doesn’t need much convincing. Not only did she release one of the best albums of 2020, she also pulled off one of the most successful livestreamed events of quarantine, when Studio 2054 had 5 million viewers tune in (by paying for tickets). The event cost $1.5 million to produce. I tuned in myself, and if my memory serves me, I paid around $20, so you can bet that her team made their money back—and then some.

Kaytranada – This may feel like a Grammys reference set-up, but I promise it’s not! Kaytranada’s last Lollapalooza performance was in 2017, and my guess is that he’s come quite the far way since then. He’s the first Black man to win the Grammy for Best Dance/Electronic Album (which is wild, considering dance music was created by Black artists), and though he was also nominated for Best New Artist, he’s certainly not new to many dance music fans.

Kygo – Another dance artist with a big 2020, Kygo seems like the logical pick for one of the other dance artists set to headline Lollapalooza this summer.

Lana Del Rey – With a critically acclaimed album from 2019 and another one releasing in just a few days, there’s no doubt that LDR would have plenty of material to play at her return in Grant Park this summer. Her last headline performance was in 2016.

Silk Sonic – While I’m not entirely sure Lollapalooza would know that Bruno Mars and Anderson .Paak would be coming together to create a super group during the months a lineup would be brainstormed and created, but I wouldn’t be surprised if they did know! With that being said, Bruno Mars is already a Lolla-veteran, and I can easily see him returning with Paak for something special.


Big Sean – I’ve admitted multiple times that I’m not up-to-date with rap music, and it’s possible that Big Sean is headliner-status, but from my understanding, Big Sean would be at that sweet spot around 7pm on a main stage before a headliner starts.

DaBaby – has any up and coming rap artist (Besides Megan) have had a year (or two) as big as DaBaby? Probably not.

HAIM – A Grammy nom for Album of the Year under HAIM’s belt, two collaborations with Taylor Swift, what else can HAIM do to be eligible for a slot on the Lolla lineup this year?

Megan Thee Stallion – Arguably the biggest artist of the past two years, this is the easiest prediction of them all.

Miley Cyrus – Who wouldn’t want to hear Plastic Hearts live? This would be a dream.

Phoebe Bridgers – There are strong rumors Phoebe was going to play Lollapalooza last year since she was touring with The 1975, who conveniently didn’t have a date in Chicago on their Spring/Summer tour. Phoebe has only gotten exponentially bigger since the beginning of 2020, so this would be a must. Edit on May 17 – Pitchfork festival announced their lineup today and Phoebe Bridgers is one of the three headliners. The festival is set for September 10-12.

St. Vincent – With a new album on the way, I can’t imagine Lollapalooza not happening without Annie. Edit on May 17 – Pitchfork festival announced their lineup today and St. Vincent is one of the three headliners. The festival is set for September 10-12.

SZA – One can dream, right?


070 Shake

Aly & AJ

Beach Bunny

Blu DeTiger

Cautious Clay

Charli XCX


Chloe x Halle

Doja Cat

Dominic Fike

Glass Animals

Greta Van Fleet

Hayley Williams

Japanese Breakfast

Jean Dawson

Jessie Ware

Lil Baby

Madison Beer

Noah Cyrus

Rina Sawayama


Tierra Whack

Zara Larsson

Check out our Lollapalooza coverage here.

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