It’s that time of the year again – Lollapalooza lineup speculation season. Convenient gaps in touring schedules, new releases and other festival lineups serve as the basis for the majority of fan predictions. With tickets and the lineup dropping in a month, social media is buzzing with fans’ hopes – some more carefully constructed than others – for who will rock the stage in Grant Park this year. Speculated acts like The 1975 and Kim Petras have already been confirmed while others,like My Chemical Romance and Rage Against The Machine, have been counted out.

Lana Del Rey

It’s been four years since Lana Del Rey made a Lolla appearance. “Norman Fucking Rockwell” came out just weeks after the fest last year, so she wasn’t able to headline. She stopped in Chicago at the beginning of November for a show at the Aragon Ballroom, but the West Coast is the only focus of her upcoming dates in the U.S. She’s secured a headlining spot for Lolla in Argentina, Brazil and Chile – so it’s pretty safe to say her name will also grace the Chicago edition of the lineup.

Billie Eilish

Billie Eilish has come a long way from her 2018 set at the Tito’s Stage. Her debut album “WHEN WE ALL FALL ASLEEP, WHERE DO WE GO?” came out in 2019 and quickly dominated the charts. She’s collaborated with long-time idol Justin Bieber on a “bad guy” remix. She’s the youngest artist to ever record a track for the James Bond franchise. Her Coachella set last year was packed to the brim, so expect a similar situation in Grant Park this summer. Not only is Eilish speculated to be on the lineup, she may just be one of the headliners – especially given the fact she’s been confirmed as a headliner for the Paris edition of the festival in July.

Lizzo

Lizzo’s last Lolla appearance was in 2018, right before her career really took off as “Truth Hurts” dominated the charts. The only thing that makes a performance less likely than other speculated acts is she’s not set to perform at any other Lolla’s this year. Despite this, the success she’s experienced alone makes her a likely candidate. Plus, like many other potential Lolla headliners, she’s a confirmed headliner at other festivals, namely Bonnaroo and Osheaga over the summer. Who knows – maybe her new friend Harry Styles will make a guest appearance at the set too, since the duo covered “Juice” at her Miami show.

Vampire Weekend

Ezra Koening promised fresh Vampire Weekend tunes at the group’s last Lolla set in 2018. With the release of “Father of the Bride”  in 2019, it’s only fitting that Koening bring the long-awaited release to fans at Lolla again. They’re another potential headlining act this year, but it really will come down to who else is announced. The group is slated to perform at every international version of Lolla, and also has spots on Bonnaroo, Governor’s Ball and Osheaga festival lineups. Plus, Chicago is conveniently missing from their list of tour dates into October.

A Day To Remember

A Day To Remember’s appearance is equally likely at either Lollapalooza or Riot Fest this year. Their newest album, “You’re Welcome,”was supposed to be released in November but got pushed back. The post-hardcore group is slated to perform at each international version of the festival, but a Riot Fest appearance almost seems more appropriate given their genre. Either way, expect to “disrespect your surroundings” at a set to remember at some point in Chicago this year.