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Highlights From Lollapalooza 2019

This year’s festival was something special as expected, with a few surprises thrown in there

Chicago is the hometown of several superstars in their own right such as Barack Obama, Chance the Rapper, and Kanye West. The city is illuminated all year with the vibrancy of a cosmopolitan mecca and the inviting nature of a small town. From music and art to food and cocktails, Chicago’s culture is effervescent to say the least. Every August for the last 25+ years, Lollapalooza has been able to strike the perfect balance between being a major music festival with a reputation that garners headliners such as Ariana Grande, The Chainsmokers, and The Strokes, and being a loyal Chicago establishment that showcases up-and-coming local bands, food, and art.

This year, the festival’s founder Perry Farrell and producers C3 Presents cooked up a few additions that aided to the festival’s general admission experience as well as VIP. The intimate stage added to the VIP North Lounge offered VIP and Platinum attendees to enjoy private shows from bands following their main sets. On Sunday, Farrell himself hosted a short performance and Q&A on the stage, where he discussed the importance of this festival to him and the city of Chicago.

Perry Farrell’s Kind Heaven Orchestra (Katrina Barber/Lollapalooza 2019)

General admission wristband-holders were given the option to upgrade to GA+ and gain access to a dedicated shaded lounge and bar (but, nothing compares to the coveted VIP/Platinum viewing deck), which helped disperse attendees throughout the festival (shorter lines and less congestion). The activations at the fest came in abundance, from Asics Underground to Revlon’s Ultra Rollerama where Ashley Graham made an appearance. Attendees escaped the heat by hanging in the Red Bull video game center hosted by Ninja and watching the pro-gamer take on special guests like Tyler Joseph from Twenty One Pilots.

Ninja and Tyler Joseph (Charles Reagan Hackleman/Lollapalooza 2019)

Standout sets throughout the weekend included Tierra Whack on the American Eagle Stage and her seriously energetic hype man, Judah and the Lion on the Lake Shore stage who kicked off their set with an immediate crowd surf from Judah Akers, and local Chicago band Beach Bunny on the American Eagle Stage who gushed about dreaming of playing this legendary fest. Maggie Rogers returned to Grant Park and belted on the Bud Light Stage, but not without the help of basically the entire festival. The witchy feminist rock star started singing “Alaska” when the sound suddenly stopped. The massive crowd didn’t miss a beat (or a lyric) and the tune was performed a cappella with Rogers joining in after gleefully taking in the magical moment.

As the sun set on Lollapalooza, attendees danced with Francis and the Lights, swayed to the dreamlike sounds of Kasey Musgraves, and finally, sang along with Ariana Grande. Grande brought out surprise guests Social House to debut their new single, “boyfriend” live for the first time, and to be honest, the boys kind of stole the stage. Their energy was electric, their chemistry was natural, and “boyfriend” slaps.

Francis and the Lights (Katrina Barber/Lollapalooza 2019)

The city of Chicago gets taken over by live music outside of Grant Park during Lollapalooza weekend, too. With official Lollapalooza aftershows featuring artists such as King Princess, Francis and the Lights, and Alec Benjamin, even if you missed the fest, you could catch some of the action elsewhere. Lolla performer Death Cab for Cutie played The Metro on Friday night with support from Beach Bunny and the guys proved that while they can command hundreds of thousands of people at a massive venue, the intimacy of a smaller stage bodes equally as well for them. The band rocked out to their new jams and at the end of the night delivered an acoustic performance of “I Will Follow You into the Dark.” The entire room grew quiet before a warm hum took over as Ben Gibbard crooned to the band’s most iconic song. When Gibbard handed the mic over to the audience, the packed crowd accepted willingly. At Death Cab’s Lolla set the following day, the band brought Chicago native Chance the Rapper on stage to perform their latest collab, “Do You Remember.”

Janelle Monae (Charles Reagan Hackleman/Lollapalooza 2019)

So, who left everything they had at Lolla? Easy. Janelle Monae proved that her artistry is unparalleled with epic costumes, production, attitude, and genuine talent. Childish Gambino made a surprise appearance during 21 Savage’s set before pouring himself into his own headlining set. But really, the attendees at Lollapalooza offered themselves fully for four days and nights, helping to secure Lolla as the premiere Midwest fest. Lollapalooza returns to Grant Park July 30, 2020 – August 2, 2020.

Main image: Katrina Barber/Lollapalooza 2019

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