Rosalía, by Dan DeSlover

With the first weekend in August quickly approaching, that means Lollapalooza 2019 is just around the corner.

Set for Aug. 1-4 at Chicago's Grant Park, the annual fest—one of the tentpoles of the festival circuit—will be headlined by Childish Gambino, Ariana Grande, The Strokes, twenty one pilots, Tame Impala, Flume and more. But as usual, there's plenty of excitement further on down the lineup.

We already know Childish Gambino will surely be one of the weekend's standout performances and Grande will most certainly deliver one of the biggest (probably with a cameo or two). twenty one pilots will bring the fire (literally). Kacey Musgraves will be stunning and Janelle Monáe will leave no doubt she's music royalty. But just below the marquee names are acts worthy of your attention. Some might even be future headliners themselves.

In no particular order:


Gabi Wilson is still riding a massive wave after winning two Grammy Awards earlier this year (including Best R&B Album). After multiple previous stints in the music industry, the past couple of years have arguably been some of her best. In fact, she opened for Childish Gambino himself this year on tour and she continues releasing new music, supported by a dynamic performance. There will be plenty sets at Lolla, but don't miss H.E.R.

King Princess

Following a breakout 2018, the singer has already been conquering this year with recent news of her upcoming debut album. Her single "1950" has become an alt radio hit, an ode to queer love and a salute to those came before her. As she continues to use her platform to shine a light in these important times, her Lolla appearance gives fans the chance to see a future star.


As Spanish language music continues to surge into the mainstream, Rosalía is absolutely one of the shining stars. Her song "Con Altura" (a collaboration with fellow Lolla performer J Balvin) is currently No. 1 in Argentina and she's coming for America next. This is not a maybe-she-will case. Rosalía is a powerhouse and her performance at Lollapalooza is for sure one you can't miss.

Lauren Daigle

The 27-year-old singer will occupy a unique space at Lolla, as one of the few if not only Christian-based artists performing at the festival. Earlier this year, she won her first Grammy for Best Contemporary Christian Music Album and her song "You Say" crossed over into pop radio, where it became a top 20 hit. She is a powerful performer and in these particularly divisive times, she'll bring a positive and welcome energy.


She appeared briefly at Lolla last year during a surprise appearance with Khalid, but this time she's got the stage to herself. And rightfully so. Last year, fellow former Fifth Harmony member Camila Cabello made her debut, and perhaps Normani's own arrival has taken a little longer, but it's definitely proof she deserves the spotlight in her own right. As she continues her solo career, this is a big moment for her.


The Norwegian artist is easily one of the most exciting voices in pop over the past couple of years. After recently releasing her breathtaking debut album Sucker Punch, the singer is heading out on her first headlining North American tour this fall. But fans at Lolla get an early preview. And while the fall trek will mostly be theatre shows, this Chicago performance allows her to prove her skill is worthy of big stages too.

Tierra Whack

Following last year's release of her debut album, she's been riding high. She even earned a Grammy nomination for Best Music Video earlier this year. And as she continues her evolution, there's no denying she brings a unique and charismatic energy to hip-hop. She's simply mesmerizing in a way comparable to Tyler, the Creator and the late Mac Miller. Her Lolla set will definitely be one of the best.

Omar Apollo

The singer already has a busy fall planned, but he gets to test out his live set a bit early in Chicago. With two projects to his name, including this year's Friends EP, he has solidified a special brand of music fusing together sounds from jazz, R&B, soul and pop. He's definitely one to watch right now.


If you ever get a chance to see Mitski live, you must. And if you're at Lolla this year, this is just mandatory. Her album Be the Cowboy was one of last year's best and she is quite plainly one of the most underrated artists making music right now. For those who missed her spring tour, this is the perfect opportunity to make up for it and catch one of the lineup's finest acts.


He may not be one of the headliners (yet), but we guarantee you there are people who bought tickets for Lollapalooza this year solely because of him. Perhaps it's not a coincidence his new album was just released. And as of this writing, Chance the Rapper's record released the same day (and had been hyped for years, practically) is only slightly ahead in the first-week sales race. Like Lolla alums Jon Bellion and Russ, NF cultivated a passionate fanbase as an indie artist, with emotional, biographical hip-hop material, and this Lolla performance likely won't be his last. Next time he'll probably just have a later time slot.