Lollapalooza 2019 Lineup: 10 Artists We Hope to See in Grant Park

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Festival season is on the cusp of hitting full swing, with Coachella and Lollapalooza bookending our favorite months of the year. We still have some time before August hits, but in the spirit of having something to look forward to, we have predicted ten artists who we hope will be included in the 2019 Lollapalooza lineup. Hit up your old roommate who lives in Chicago and secure a place to stay, because if our forecast is correct, you will not want to miss this one. Based on the all of the artists we have been following this year, here are our 2019 Lollapalooza lineup predictions.  


King Princess

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The fiercely unfiltered king of pop seems to be on a roll lately, scheduled to play Coachella, Boston Calling, The Governor’s Ball, Bonnaroo and Firefly—pretty much every major festival offered in the US this coming summer. We hope King Princess makes it onto the Lolla list as well, because we love it when she plays “1950.”


boy pablo

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If you love bedroom pop, odds are you’ve got a thing for boy pablo. The Norwegian lovechild of Mac DeMarco and Omar Apollo, boy pablo is hard to quit once you’ve started. Scheduled to play Coachella this April, we’ve got a hunch that boy pablo will also be gracing the Lollapalooza stage this year.


Ella Mai

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The rising R&B songstress stole our hearts with her self-titled album earlier this year, and swept awards season with a Grammy for Best R&B Song and a nomination for British Breakthrough Act. Ella Mai will be stateside in the days leading up to Lollapalooza, playing Mo Pop Festival in Detroit. We’re taking that as a sign she’ll be hitting Lolla as well.


Conan Gray

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We have developed a serious crush on Conan Gray over the past year. The YouTuber-turned-pop sensation dropped jaws in 2018 with his Sunset Season EP, using his sense of humor and powerful voice to comment on issues plaguing the modern coming of age story. 2019 has seen Gray make his late night television debut, hitting the tour circuit hard with another one of our favorites, girl in red.


Juice WRLD

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If you’re unsure about who Juice WRLD is, let us assure you—you’ve heard his music. His song “Lucid Dreams” is closing in on a billion streams on Spotify alone, and his latest album Death Race for Love has just as much potential to go viral. His sad boi, autotune-heavy music is a hybrid of pop and hip-hop and will get you deep in your feels. Currently on tour with Nicki Minaj, Juice WRLD is an undeniably strong candidate for Lollapalooza 2019. Did we mention that he is from Chicago?


Lennon Stella

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Lennon Stella first graced the internet doing covers with her sister as part of the duo Lennon & Maisy. With a decade of experience and an unbelievable glow-up under her belt, Stella is now pursuing her solo career (and absolutely killing it might we add). Stella’s debut EP Love, me showcases her distinctly husky vocals and dark pop sensibilities. Cross your fingers for a Lollapalooza performance from the rising songstress.


SG Lewis

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Electronic producer, songwriter, and crowd favorite SG Lewis has been hard at work, most recently releasing his single “Throwaway” with Clairo. Lewis has amassed millions of streams across platforms and is set to play Coachella this year, with fans eagerly anticipating his danceable, high energy set. We’re hoping to catch him at Lolla before he heads to overseas to play Boardmasters Festival in the UK.


Dominic Fike

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The man that sparked a label bidding war before ever releasing music is now playing live. Dominic Fike has accumulated quite the cult following since the release of his debut EP, Don’t Forget About Me, Demos but remained shrouded in mystery until recently playing his first shows. He doesn’t currently have tour dates released to the public, but we’re hoping to see him play in Chicago this August.


Pink Sweat$

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To say that Pink Sweat$ is our hero is an understatement. The unapologetically sensitive R&B singer is vocal silly putty, with the ability to hit impressive falsetto notes with ease. His artistic vision comes in the full package, from sonic delights to moving music videos. Pink Sweat$ needs to play Lollapalooza just so we can see the pink outfit he puts together for his performance.


Tierra Whack

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Let’s be honest—it’s Whack’s World now. Tierra Whack both confused and delighted audiences with her debut concept album Whack World and accompanying collection of music videos. Since then, Whack has been playing shows nonstop, and we have a feeling she isn’t going to stop at Coachella. 

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