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The Most Painful Scheduling Conflicts at Lollapalooza 2019

The Lollapalooza 2019 schedule is finally here after what seems to feel like a chaotic mess of a rollout for this year’s festival. Tickets have still not completely sold out and the promotors waited nearly a month to release 1-day tickets after 4-day passes took extremely slow to sell (they have not sold out yet).

I expected them to wait even longer to release the schedule, to be honest, but maybe this is a tactic that they hope will help push ticket sales? To me, that would make the most sense, since people want to know who they are able to see after dropping over $120 for a day pass and nearly $400 for a 4-day. Others of us (like myself) are just sorta crazy and decide to buy the passes when we don’t even know the official lineup yet.

Below are my picks for the hardest conflicts of the lineup and who I’m likely going to choose to see over the other. This sucks and happens every year – but that’s unfortunately the way the game works when you’re like me and genuinely have interest in the majority of the lineup.


Lennon Stella, 2:45-3:30pm, half.alive, 2:50-3:30pm, Harry Hudson, 3:20-4pm

THREE artists I wrote about in my post so Lolla sorta did me dirty with this. Lennon has some of my favorite songs released this year so I will be prioritizing her set for sure, but each of these artists have such different sounds it’s sad that I have to make such a tough decision, though they are playing at the same time for that very reason. I think Lennon will have a big crowd pull on the main stage but I’m curious to see if that actually happens since it’s before 3pm and on a Thursday, in my experience the festival is really quiet on Thursday and Friday before 4 or 5pm.

Who should you see? Pop fans – Lennon all the way. She has a great voice. half.alive has had a really fast rise to fame and will likely have a decent crowd and is on a fun stage in the shade. Indie/alt R&B fans – go to Harry Hudson. He’s a frequent collaborator with Jaden Smith – maybe he’ll show up for a surprise appearance.

H.E.R., 4:45-5:45pm, Cautious Clay, 5:15-6pm, Hayley Kiyoko, 5:45-6:45pm

H.E.R. just won a grammy, so it would have been really cool to see her perform at such an important time in her career. I’ve seen Cautious Clay before but was really curious to see how he’s grown as a performer since then. Hayley has some bops and overall seems like a really great person. As I type this I have no idea where I’m going to end up. Maybe a bit of all three?

Who should you see? H.E.R. is going to pull a massive crowd. Cautious Clay plays a variety of instruments onstage. Kiyoko will probably pull the kids who know 2-3 songs (honestly me) and definitely will be congested as people will be headlining that way to see Hozier after directly after her. So if you don’t like the massive crowds, maybe check out Cautious Clay?


Japanese Breakfast, 3:45-4:45pm, Sigrid, 4-5pm, Tierra Whack, 4-4:45pm

This hurts. It really does. I have just been getting into Japanese Breakfast as of lately (I’ve heard her before but her more recent stuff is starting to stick more than the old) and Sigrid and Tierra Whack are another two artists I highlighted in my previous post. I love both of these women and I sadly will probably choose Tierra Whack over Sigrid because I think her music is unprecedented, but it’s definitely a choice I will be contemplating until August.

Who should you see? If you want an upbeat pop show, see Sigrid. If you want to chill and drink a beer, Japanese Breakfast. If you want to be a little weirded out and get a little rowdy, see Tierra Whack.

Death Cab for Cutie, 6:45-7:45pm, Janelle Monáe, 6:45-7:45pm

DCFC and Janelle couldn’t be more opposite, but believe me when I say that I have waited YEARS for a chance to see Death Cab live and I will be missing it again this year. I was such an #emo kid when I was in my early teens and LOVED their music, and I’ve missed every opportunity I’ve had to see them perform in Chicago. But Janelle delivered one of the best albums of 2018 and I want to see her perform a lot of it while I can, before she starts working on a new album and stops touring on Dirty Computer. Plus I Just feel like DCFC is touring a lot more often than she is.

Who should you see? Janelle Monaé is going to have one of the best sets of the entire weekend. Sorry, DCFC – I still <3 you.


Sam Fender, 1-2pm, Men I Trust, 1:45-2:45pm, Bea Miller, 1:50-2:30pm

These are three more artists I wrote about in my 20 Acts to See so this HURTS. I have been obsessing over Sam Fender’s music for the past few months so he’s definitely the one I am going to prioritize, but Men I Trust has such cool vibes and Bea Miller has really catchy pop music and a great voice. I will probably end up seeing Sam and then the end of Men I Trust, so it’s not entirely a lose lose.

Who should you see? Sam Fender is going to explode in the next year. I am calling it now.

Mondo Cozmo, 2:45-3:45pm, Jade Bird, 2:50-3:30pm, Bad Suns, 3-4pm

I’ve seen Mondo Cozmo at Lolla before and they were fun, but definitely more of a lax environment and pulled a lot of the older crowd. I wouldn’t plan to see them again, but I imagine they have a huge overlap in fans with Bad Suns, so it’s weird to me that they’re on at the same time. I plan to definitely start with Jade Bird and depending on how that goes, will either stay for all of her set or leave early to see the rest Bad Suns’ performance. I’ve raved about Bad Suns for years and just saw them, so I would much rather see someone I haven’t seen who I’ve also been really loving for the past year or so. It’s really great to see that they are on a main stage, too!

Who should you see? Folk pop – Jade Bird. Her vocals are awesome. Fans of classic rock with some 2019 flair – go to Bad Suns.


Denzel Curry, 5:15-6pm, Sharon Van Etten, 5:30-6:30pm, Rosalía, 6-7pm, Kacey Musgraves, 6:30-7:30pm

While you can see that not all of these artists clash, they do essentially all clash with each other. While putting Denzel & Sharon against each other seems reasonable since they are entirely different artists and probably don’t share much overlap in terms of fans, a clash between Rosalía and Kacey seems rough. I am not too familiar w/ Rosalía’s music but I know she’s going to have a big 2019 and I definitely would have considered checking out her set if there weren’t conflicts. I expect to be some fan overlap between her and Musgraves, so that’s unfortunate. I am just happy that Van Etten, Musgraves and Mitski don’t overlap as those are three women I’m really looking forward to seeing on Sunday, and especially neat to see another female (Ariana) closing out the weekend.

Who should you see? If you were me…20 minutes of Denzel, 45ish minutes of Sharon, all of Kacey. She just won Album Of The Year!

Click here to read my post on 20 Artists To See At Lollapalooza 2019.

Happy Lolla!

  • Kristin

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