Top 10 Lollapalooza picks: Miley, Megan, Tyler, alt-rock origins and more must-see sets

Lollapalooza Top 10 Photo by Daniel DeSlover

Against all odds, the 2021 edition of Lollapalooza is finally here, and besides marking a comeback following a pandemic-induced closure, it also marks the usually annual event’s 30th anniversary.

With that in mind, the mega-festival dug deep into its bag of bookings for the top of today, a few old schoolers and future glimpses of greatness, all coming to Grant Park from July 29 through August 1 for the vaccinated or those who present a negative test.

So head downtown for what’s quickly shaping up to be the event of the summer and don’t miss any of these must-see sets from familiar faces and perhaps a few who are less obvious, representing pop, rock, rap, electronic and hybrids of them all.

Lollapalooza Top 10

Photo by Andy Argyrakis

1. Miley Cyrus (Thursday)
Pop/rock/country superstar Miley Cyrus has reinvented herself almost as much as Madonna and its essential to see what rabbit she’ll put out of a surely outrageous hat once the “Midnight Sky” starts rolling into view for the ultimate “Party In The U.S.A.”

2. Foo Fighters (Sunday)
Few alternative rock bands have been able to transcend generations to degree of the Foo Fighters, which is why Dave Grohl, formerly of Nirvana, and the guys are ideal choices to mark this milestone occasion.

3. Megan Thee Stallion (Saturday)
Hands down the hottest rapper in the game right now, Megan Thee Stallion is destined to slay and show Chicago exactly why everyone from Beyoncé to Cardi B is getting on board.

4. Journey (Saturday)
Will Steve Perry show up? As classic rockers Journey would say, “Don’t Stop Believin’,” but it’s safer to bet on the newly revamped line-up of long timers Neal Schon, Jonathan Cain and Arnel Pineda, alongside the return of “American Idol” judge Randy Jackson with newcomers Narada Michael Walden and Jason Derlatka.

5. Tyler, The Creator (Friday)
After recently dropping “Call Me If You Get Lost,” Tyler, The Creator cemented his place as a rap and hip-hop visionary coming off a decade of solo game-changers, plus prior time with the now classic collective Odd Future.

6. Cash Cash (Thursday)
The DJ trio known as Cash Cash brings a bounty of beats, from club-packing originals to blockbuster remixes for the likes of Britney Spears, Lady Gaga, Bruno Mars, Pink, Katy Perry, AJR, Capital Cities and Icona Pop.

Lollapalooza Top 10

Photo by Daniel DeDeslover

7. DaBaby (Sunday)
Rapper DaBaby continues to rack up a string of multi-platinum singles on his own and as a frequent feature for fellow Lolla performers Post Malone and Megan Thee Stallion, along with alumni like Dua Lipa and Camila Cabello.

8. Jimmy Eat World (Thursday)
Another blast from the past that remains relevant is emo/alt-rockers Jimmy Eat World, whose landmark “Bleed American” album, responsible for the ubiquitous “The Middle” and “Sweetness,” just turned 20.

9. Brockhampton (Sunday)
Boasting an array of cultures and orientations, Brockhampton is hands down the most diverse hip-hop act in history and packed with tons of talent, so much so that the guys may be going their separate ways after this tour behind “Roadrunner,” which only ups the essential factor.

10. Aly & AJ (Thursday)
Sister pop duo Aly & AJ is back with their first full-length collection since 2007 thanks to the tongue-twister, “A Touch Of The Beat Gets You Up On Your Feet Gets You Out And Then Into the Sun,” which may as well foreshadow what’s bound to happen all weekend!


Lollapalooza comes to Grant Park Jul. 29 through Aug. 1. For additional details, visit Lollapalooza.com.