Lollapalooza 2019 Predictions & Rumors

Lollapalooza 2019 predictions and rumors.

Surprise! It’s never too early to start throwing out predictions for Lollapalooza. Last year I started my list in November – this year I’m coming in hot even earlier.

As usual, these predictions are based off of my own research and buzz on the Lollapalooza Reddit thread. I don’t and will never take all credit for these predictions on my own. I read a lot and form predictions based on who I listen to on my own.

I’ll let readers know every time this post is updated, but it has officially started on October 2, 2018.

UPDATED on March 19 with confirmed artists that Lollapalooza shared on their YouTube page at 2pm CST.


Childish Gambino – He hasn’t been at Lollapalooza since 2014. We usually share one headliner with Coachella and I don’t see us getting Kanye or Justin Timberlake. (EDIT – I think this is more unlikely and it will be Ariana instead of him). 

Florence & The Machine – Hasn’t been since 2015 – and back then her set was cut short due to weather. We need more female headliners and she would be a perfect fit – she released new music this year. (Playing a show here in May – likely out)

Lana Del Rey (Added 1/11). New music coming out. Can draw a crowd similarly to FATM. I would have to assume it’s one or the other. 

Twenty One Pilots – Since their last performance in 2015 – they’ve blown up IMMENSELY. Ridiculously so. It’ll be interesting to see where they land in the next few months since their new album is coming out soon – but they’re currently selling out another arena tour.

The 1975 – Coming back strong promoting their 3rd studio album, out on November 30. They subbed in 2016. I can see them headlining on Thursday night.

Weezer – If Lolla continues booking a couple rock artists as headliners in the past years like Blink 182, The Killers, Arctic Monkeys, etc, Weezer makes the most sense. They also probably aren’t as expensive to book compared to a legacy rock act. (1/11 – this seems possible but not sure based on booking trends for other festivals this summer). 

Mumford & Sons (Added 11/5). Playing Chicago end of March, have international festival dates on their tour into the summer. Haven’t played since 2013.

Foo Fighters (Added 1/11). They have openings between June and mid-August. They haven’t played Lollapalooza since 2011.

Tame Impala (Added 1/11). Insider info here saying multiple sources have confirmed it.

Other headliners – we need at least one EDM artist, another rapper, and probably one big mainstream artist. I would love for the mainstream artist to also be female (cough cough, Lady Gaga) – but we’ll see. Who else is big in EDM currently? I have no idea. As for rapper, everyone always wants to throw out Kanye – so we’ll see about that – but Kendrick Lamar or Cardi B? would seem more likely IMO.

My most likely headliners as of 1/11 (in no perfect order)

Foo Fighters / Kendrick Lamar / Childish Gambino / Tame Impala / Twenty One Pilots / Florence & The Machine OR Lana Del Rey / EDM ARTIST / The 1975 

UPDATE 1/15:

It’s basically been 100% confirmed that Ariana Grande is headlining Lollapalooza. This throws things off a lot. Here’s my new Top 8 as of yet:

Ariana Grande / Foo Fighters / Tame Impala / Twenty One Pilots / RAP ARTIST / Florence OR Lana / EDM ARTIST / The 1975

This is becoming a messy prediction for a top 8, tbh. 

EDIT on 1/23

The 1975 is likely to be out. They just announced another date in Europe on August 1. It’s extremely unlikely for them to play that show, fly to Chicago for Lolla, and fly back to Europe. Oh well!

I’ve also been reading that it does seem possible for us to share 3/3 of Coachella’s headliners, which is unprecedented. Here’s what I’m thinking:

Ariana Grande / Foo Fighters / Childish Gambino / Tame Impala / Twenty One Pilots / Florence OR Lana / Cardi B? /  EDM ARTIST 

Here’s my final pick for Top Two Lines as of 3/4/2019. No changes will be made to this unless there is a huge bomb dropped between now and when the lineup is due to be out (likely on March 26th). I’ll explain the new additions.

Ariana Grande / Childish Gambino / Twenty One Pilots / Tame Impala
/ Cardi B / The Lumineers / A$AP Rocky / Kygo / Death Cab For Cutie

  • The Lumineers has been heavily rumored across a lot of websites including the Reddit thread. They have not played since 2013 and they drew a MASSIVE crowd that day. They took a long hiatus but are back now and have been teasing new music. Though I don’t love the idea of them headlining a night, I think they will pull a crowd. OUT as of 3/11 -playing Piqniq. 
  • I have no real explanation for A$AP besides the fact that he has been thrown out recently and Lolla definitely needs another rap artist in their top line. Gambino’s more recent music is more R&B heavy and Cardi B., although a rap artist, will pull the audience of a pop artist. I think she will get an insane pull. A$AP has a break in his tour dates between July 20 and August 16, but he’s in Spain then Finland…he could easily come back to the states but it’s still something to point out.
  • Kygo fills that spot I left open for an EDM artist. I know nothing about Kygo but he has openings in his touring from end of June to mid August. 
  • Death Cab For Cutie is another name that’s been floating around a lot and they definitely fit the rock pull that Lolla seems to be attempting to get back to with previous year’s acts like Arctic Monkeys, Vampire Weekend, Arcade Fire, etc. They are about to start a tour at the end of the month and are conveniently skipping Chicago and the closest show to IL is Summerfest in July. 

UPDATES on 3/11.

The Lumineers are playing Piqniq on 6/15. I really don’t know who else is going to be a headliner in their place so I’m going to leave it blank for now.

If my headliners are correct (minus The Lumineers), this is what I predict will happen in terms of who is playing what day. This is based on last year’s lineup order and what days they ended up playing. This is ENTIRELY SPECULATIVE. I’m thinking the blank spot could possibly go to The Foo Fighters?

Thursday – Tame Impala (North) vs. Cardi B. (South)
Friday – Childish Gambino (South) vs. ___________ (North)
Saturday – Ariana Grande (South) vs. A$AP Rocky (North)

Sunday – Twenty One Pilots (South) vs. Kygo (North)


There’s someone who is 150000% certain that the artists below are the top four booked. We have less than 48 hours until we’ll know for sure, but it’s fun to speculate. 

Here’s my new top predictions (not entirely different) 

The Strokes / Ariana Grande / Childish Gambino / Tame Impala / Twenty One Pilots / Cardi B / A$AP Rocky / EDM ARTIST (potentially Disclosure/Kygo/Alesso)? 

My reasoning: That top four seems pretty likely at this point. Disclosure is a new name that popped up as a rumor and they seem especially likely after not appearing on this year’s Spring Awakening festival. Alesso was one of the confirmed artists on Lolla’s IG story (they’ve been teasing artists every day for the past 5 days or so).

All confirmed artists via Lolla’s IG stories and their YouTube page as of 3/19. Asterisks mean they were also in my list of predictions.

  • AJR
  • Alesso*
  • Calpurnia
  • Chelsea Cutler*
  • Crizzly
  • Fisher
  • Gunna
  • Hayley Kiyoko 
  • Isles
  • Janelle Monae*
  • J Balvin
  • Lil Baby
  • Lil Skies
  • Lil Wayne
  • Louis The Child
  • Madeon
  • Normani*
  • Pink Sweats
  • Rosalia
  • Rufus Du Sol*
  • Slash
  • Svdden Death
  • Tame Impala*
  • Tenacious D
  • Tierra Whack
  • Yaeji

Stay tuned for the lineup drop!




Anderson .Paak – Just played Lollapalooza Brasil and Argentina. From my research I can’t find any evidence of him playing Lolla Chicago ever. His newest album was released on 11/16. (OUT – has his own show in Chicago in June)

Hozier – He played way back in 2014 just a couple months before his debut was released and I’m STILL mad that I didn’t know about him back then. With a new EP released and tour dates this fall, I’d be beyond SHOCKED if he doesn’t land on the lineup this year. I need this.

Janelle Monaé – Her album came out this year in April so it was more unlikely for her to be on this year’s lineup and it makes more sense for her to be on it in 2019. Her album is going to end up on everyone’s “Best of” lists in a couple months and I can see her closing out a side stage this year, similar to the time and stage Dua Lipa played this year.

James Blake – I’d say this a wildcard, but Pitchfork is not a fan so he won’t be performing there. His Chicago show is in March – plenty of time to make his way back this August.

Kacey Musgraves – I’m almost positive she’s never played Lollapalooza and she is now slated to perform at Coachella. Her 2018 album Golden Hour is up for AOTY at the 2019 Grammy’s. Lolla tends to get a couple country performers every year, and with Musgraves’ crossover success, this booking would make sense.

Kid Cudi 

SZA – Was heavily rumored to be performing last year. Is this year her time? Hasn’t played since 2015.

Young The Giant – I’m pretty sure that I’ve predicted them to be on the Lolla lineup for multiple years in a row and they still HAVE NOT appeared since 2014. Their new album is out in a couple weeks so I will be SO salty if I am wrong AGAIN. If they subbed before The 1975 I would be a very happy lady. (Update on 2/19 – they announced a tour w/ Fitz & The Tantrums and Coin with no date in Chicago – seems like we’ll likely get all three). ANOTHER update on 3/11 – playing Piqniq on 6/15. They’re out again and I’m annoyed.

General Lineup:

Alec Benjamin

Alessia Cara – Played Lolla in 2016 after her breakout year. Now she has a Grammy and her sophomore album is set to release on 11/30.

Alice Merton

Anna Of The North – Just opened for LANY on tour.

Aurora – Played in 2016, released another album, going on tour early this year. Has a show in Chicago in early March.

Betty Who – Last played in 2014 and she’s skyrocketed since then. Has been consistently releasing new music this year and is about to tour with Panic At The Disco.

Bob Moses – Another name I’ve seen all over the place but I actually know their stuff. Super mellow house music.

boy pablo 

Broods – They seem like their career has been at a standstill for years but now they’re opening up for Taylor Swift on the Australian & NZ leg of her tour – so maybe this is opening doors for them. EDIT – Their next album is out in Feb. 

Carlie Hanson – Played Mamby On The Beach in 2018, her biggest song is at 48 million streams…need I say more?

Cautious Clay

Charli XCX – (OUT – P4k)

Charlotte Lawrence – I think she could have performed this year but she’s still developing her sound and doesn’t have an album out yet. If she’s releasing something in 2019 I can see her performing on the BMI stage.

Chelsea Cutler – Playing a show in Chicago this Feb. and sold it out pretty fast.

Christine & The Queens – Though I can see P4K being far more her scene.


Courtney Barnett 

Ella Mai

Elley Duhé 

Fitz & The Tantrums

Grandson – His political music has been BLOWING UP towards the end of the year and I can see him really making a splash in 2019. He’s also currently touring with Nothing But Thieves and they’re Lolla veterans. Grandson played Mamby On The Beach in 2018.

Hippo Campus – They last played in 2017 and their new album was just released. If it gets enough traction they’ll be back (it’s one of my favorite albums of the year!)

Hobo Johnson – I haven’t heard one song by this dude but his name has been all over the place.

Jade Bird – Another person who could have played in 2018 and she even played Bonnaroo this year. We’ll see if Lolla snatches her next year – hopefully an album will be out by then. EDIT – Touring with Hozier. Said tour is NOT hitting Chicago. I tweeted that this probably means they’re playing Lolla. Jade Bird favorited the tweet and replied to it with a wink. Need I say more?

Japanese Breakfast 

Jeremy Zucker – He’s had a huge year and I can see him performing around the time that Lauv did this year. Similar sounds too.

Juice WRLD

Kim Petras – Very Charli XCX and just released new music. Currently touring with Troye Sivan.

King Princess – Another person I’ve loved this year. She’s only released an EP but I can see her becoming a lot bigger next year.

LaLa LaLa – A Chicago artist whose debut came out this year. Could be at P4K. (OUT – P4k)

The Lemon Twigs

Let’s Eat Grandma – Could be Pitchfork’s booking.

Lucy Dacus

Maggie Rogers – Just came off of her SNL debut performance. EDIT: Playing Coachella. I’d say she’s a shoe-in for Lolla.


The Marías – Completely exploded this year and have never played Lollapalooza.

Marina (Formerly Marina & The Diamonds)

Mitski – Be The Cowboy was the best album of the year. She could easily perform at Pitchfork in 2019 but anything is possible this early on in the game.


Omar Apollo 

Parcels – Their debut album rocks and they’re playing Coachella as well as a show in Chicago in early March.

Rufus Du Sol 


Snail Mail – Similar to Mitski – she can land on Pitchfork’s lineup. She’s been in Chicago multiple times this year and will be back again in January for a show at The Metro. She’s another person who has had a critically acclaimed album this year. (OUT – P4k)

Sofi Tukker 

SOPHIE – She’s playing Coachella and can easily land on Pitchfork’s lineup as well, but I’d say it’s a toss-up.

Sundara Karma – Doing pretty well in the UK, I saw them perform in 2017 at a super small venue in Chicago. Their second album is coming out on March 1 of next year.

Sunflower Bean 

Unknown Mortal Orchestra

U.S. Girls – I definitely think they’re going to play Pitchfork but it’s literally a toss-up with a handful of artists every year as I’ve been saying.


Wolf Alice 

Yellow Days

070 Shake

Stay tuned for continued updates! Subscribe via email to be the first to know when I’ve shared something new.

Lolla 2016 Predictions
Lolla 2017 Predictions
Lolla 2018 Predictions 

Click here for all of my Lolla coverage.

– Kristin

2 comments on “Lollapalooza 2019 Predictions & Rumors

  1. If any of those predictions are true, Lollapalooza 2019 will be incredible!! x

  2. Pingback: Lollapalooza 2020 Predictions & Rumors – Chicago Haze

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