Lollapalooza 2019: Best days to go, top acts to see at the Chicago mega festival

Piet Levy
Milwaukee Journal Sentinel
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Childish Gambino headlines Lollapalooza in Chicago Aug. 2.

Here's something we didn't expect to write right before Lollapalooza: Tickets are still available. 

Two years ago, the Chicago festival sold out all of its four-day passes 2½ hours after they went on sale — par for the course for one of the top destination festivals in the world.

The dramatic sales slowdown probably says more about consumer interest in festivals and the saturated marketplace in the Midwest than the lineup, which boasts Ariana Grande, Childish Gambino, Janelle Monáe, Twenty One Pilots and 177 other acts.

So instead of scouring for a secondhand pass, you have the luxury of getting one at face value. Or you can save even more money and pick just one day for your Lollapalooza adventure.

Which day should that be? Of course we have an opinion. 

Aug. 1

The Chainsmokers headline Lollapalooza's first night Aug. 1.

Marquee names: The Strokes, The Chainsmokers, Hozier, Rufus Du Sol, H.E.R.

Top acts: Christian crossover artist and powerhouse vocalist Lauren Daigle; promising possible future pop star Hayley Kiyoko; Saba, a shining force in Chicago's rich hip-hop landscape.

Lineup ranking: Worst of the four days. Despite buzzy artists like recent best new artist Grammy winner H.E.R., Daigle and Kiyoko, their limited discographies make the $130 base rate for general admission Thursday hard to justify, especially since the night ends with the Strokes (meh) and the Chainsmokers (ugh).

Aug. 2

Janelle Monáe is likely to put on one of the strongest sets at Lollapalooza in Chicago this year.

Marquee names: Childish Gambino, Tame Impala, Janelle Monáe, 21 Savage, Death Cab For Cutie

Top acts: Livewire rapper and singer Tierra Whack; Pharrell Williams-approved pop artist Maggie Rogers; invigorating indie-rocker Japanese Breakfast.

Lineup ranking: Monáe is likely to be the highlight of Lolla 2019, and the night ends with two of the most anticipated headliners with Gambino and Impala (and the most aggravating schedule conflict of the weekend). Combine that with undercard heavyweights like Rogers and cutting-edge newcomers like Whack, Friday is Lolla's best day this year. 

Aug. 3

J. Balvin will be the first artist who sings entirely in Spanish to headline Lollapalooza in the festival's history.

Marquee names: Twenty One Pilots, J. Balvin, Lil Wayne, Gary Clark Jr., Tenacious D

Top acts: Scarypoolparty, stage name for guitar master and recent "American Idol" standout Alejandro Aranada; Fantastic Negrito, who overcame a difficult childhood and near-fatal car crash to become a decorated R&B act and inspired live performer; Jade Bird, an English Americana artist who held her own opening for live show titans Father John Misty and Jason Isbell this summer. 

Lineup ranking: Third of four. It's not a weak day by any means, but considering Saturday is the only day when all single-day tickets are sold out, it's going to be the most crowded, and the cost for resale tickets is likely to be higher. 

Aug. 4

Top-of-the-bill headliner Ariana Grande will close out Lollapalooza in Chicago Aug. 4.

Marquee names: Ariana Grande, Flume, Kacey Musgraves, Meek Mill, Perry Farrel's Kind Heaven Orchestra

Top acts: Guitar great Slash, of Guns N' Roses fame, will be performing with Myles Kennedy and the Conspirators; Rosalia offers a fresh take on flamenco, drawing from pop influences; Indie rocker Mitski, whose newly theatrical live sets match the raves for last year's "Be the Cowboy" album.

Lineup ranking: Second. Whereas the energy at Lolla tends to peter out by the last day, the festival has an exciting cluster of diverse acts at the very end, spanning from rock to Latin to pop to hip-hop to country to EDM. And if for some reason you have "see NBA great Shaquille O'Neal perform a DJ set" on your bucket list, you'll have a chance to do that, too. 

The Journal Sentinel will be covering all four days of Lollapalooza 2019. Check back for coverage at

Contact Piet at (414) 223-5162 or Follow him on Twitter at @pietlevy or Facebook at

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