Along Chicago’s Michigan Avenue, groups in a bizarre range of outfits pass by sipping from the straws of their hydration packs in between fast and excited banter, rushing to a gate entrance nearby. I see walking basketball jerseys, long hair braids, fishnet tights, white Nike Dunks and glitter gracing young, rosy cheeks—there’s always lots of glitter.  

There’s a certain excitement in the air. Grant Park is lined with tall, wired fences and huddles of Chicago police officers. My entrance is all the way at the south end, on 11th Street, so I try to walk most of the way on Wabash, a little removed from the crowds. But as soon as I hit Michigan, people call out to me: “Cold water! Cold Beer! Gatorade! It’s cheaper out here than it is in there!”  

I’ve been asked before, by someone waiting at the crosswalk with me, what was going on at Grant Park. It’s hard to believe at this point, after Lollapalooza’s 20 years at the park grounds in Chicago, that some people might not be in the know. It’s one of the world’s largest music festivals that attracts around 400,000 people each year. In 2023, the festival contributed $434 million to the City of Chicago and supported the equivalent of 3,197 full time jobs. The festival also generated $6.8 million in amusement tax revenue for the city.  

I’m not new to the festival, having attended every year since 2017—except for 2020. In 2019, I covered the festival for the first time at 20 years old and now feel a sweet comfort about the annual fest, knowing the faces I will see and catch up with in the press tent. But this year, I wanted to experience the festival as though I had never attended it before—with an open and curious mind, ready to take advantage of the slew of offerings, experiences and music across four sweaty, music-filled days.  

Q101 pop-up with Wilderado  

At 12:30 p.m. on Thursday, I rolled up to Reggie’s on South State Street expecting to see a long winding line in front of the venue. To my delight, I was the fourth one there—eager to see one of my favorite bands, front and center. The day before, Tulsa, Oklahoma, rock band Wilderado announced a free pop-up show with Q101 WKQX, a local Chicago radio station. As one does, I immediately signed up and changed my first day plans to catch their set. It was my sixth time seeing them live, and it was by all means my favorite show I’ve seen from them.  

For a sold-out show, Reggie’s can only fit just over 100 people. At Wilderado, there at most 40 people in attendance—but hey, they announced it just the day before and it was on a Thursday in the middle of the workday. A 7-Up in hand, I twiddled my thumbs for a good hour and half before the band went on stage, sitting in a perfectly air-conditioned concrete setting.  

Anytime Wilderado comes out on stage, I can’t help but laugh—mostly because singer Max Rainer is this towering man with awkward stature. He’s so personable and inviting, and he always looks a bit nervous. But each time I see them live, he gains slightly more confidence. With his guitar in hand, he dove into Stranger, which I can always tell is going to be the one they start with. On their live album, it’s the first song on the track list, which was coincidentally recorded live in Chicago at Thalia Hall—the first show of theirs I’d attended.  

Wilderado have a calming, upbeat folk-rock sound with Rainer and Tyler Wimpee on vocals and guitar, Justin Kila on drums, plus a touring bassist. The band know when to glide the crowd along in a softer acoustic-driven ballad like their latest single Sometimes. But they also know how to amp it up a notch. With songs like Morning Light, Rainer gives his best alternative scream during the chorus.  

With a smaller crowd in attendance, Rainer took the time in between songs to banter with the crowd and make the experience more personal. Last year he was asked to sing vocals for a song in the new movie Twisters, which he admitted he did in about 15 minutes—his vocals ultimately ended up on the song Wall of Death with Ken Pomeroy and James McAlister, a cover of the Richard Thompson song. He also ended up in the movie playing the song alongside the others, which he said took about eight hours to finish shooting. And yes, he did meet the cast.  

Admitting to a bit of nerves ahead of their Lollapalooza performance on Friday, Wilderado lets the crowd in at the shows in a way that feels like your friend opening their arms to you. They’re a southern comfort that’ll make you feel whole. The band’s second studio album Talker is set for release on Sept. 20 via Bright Antenna Records.

Midday Jungle 

I made it to Lollapalooza festival grounds just after 4 p.m., much later than I’m used to. With only a few minutes to spare, I ran toward the Bud Light Stage to catch Jungle, a groovy British dance rock band—as more than half of the festival attendees walked in the opposite direction toward Chappell Roan. I always experience dilemmas at the festival: Which band to see? Which artist am I okay skipping? Does it make sense to run all the way across the festival to catch a few minutes of this set? Despite not being a headliner, Chappell Roan pulled in the largest crowd I have ever seen at a festival, with thousands of attendees adorned in pink cowboy hats and bandanas, glittery, lacy corset tops, flowy white skirts and calf-length cowboy boots. She’s bound for headliner status!

I settled on going in the opposite direction of the massive crowds and seeing Jungle for the first time.  

Despite the struggle to get through flocks of people, there was still a huge turnout for Jungle’s set. Way too many people are allowed to attend this festival. But, I put some pep in my step as I saw people dance-running to the stage, their music undeniably groovy and demanding movement.  

I don’t often listen to the genre, but Jungle’s tunes are a great entrance into fun dance music meant for letting loose. They’re very rock-driven, with tangible percussion, guitars, vocals and splashes of catchy synth. Jungle reminds me why I enjoy festivals. They demand attention because it’s fun, carefree, groovy music that I wouldn’t have otherwise sought out. After seeing them perform live, I’m eager to seek them out again.  

With multiple vocalists, the band has beautiful harmony. And despite warnings of thunderstorms all day, it turned out to be a wonderfully hot and sweaty early evening set. They all looked like the coolest band you know—sporting elegant sunglasses and flying through their set with ease.  

Toward the end of their set, vocalist and multi-instrumentalist Lydia Kitto brought out the flute and the crowd went wild. There’s nothing better than when a musician brings out an instrument people aren’t used to seeing in the mainstream. And she sure could play that flute.  

Dream house 

Every year, Lollapalooza features artists I have listened to here and there but have never seen live. After Jungle’s set, a mound of clouds offered some needed relief from the sun as English indie pop musician the Japanese House (Amber Mary Bain) took the stage. It’s soothing, dream-like music with intricate piano and synth, and soft ethereal vocals. The band is reminiscent of bands like Crumb, who have that peaceful, psychedelia vibe that makes you feel like you’re floating on a cloud—only the Japanese House is a lot more rock-driven.  

The band has an interesting budding head dynamic live that works seamlessly, offering vibrating bass and guitar riffs in toe with humming vocals and keys. Vocals are smooth, but they sound like they might have a delay effect or some kiss of autotune in there—to get this slight interval in production. It adds to the airy vibe. The Japanese House are like a mixture of bands Boygenius and The 1975. 

During one of their most-recognized songs, Saw You In A Dream, Bain humorously fumbled with the lyrics and had to start it over, coolly bringing it back into focus.  

Jam-packed grounds 

If you’ve never been to Lollapalooza, imagine the busiest place you’ve ever been and triple that number. After skipping a year of the festival in 2020 because of the COVID-19 pandemic, the festival has since opened its doors to more attendees. On any given day throughout the weekend, more than 100,000 people pack the festival grounds. And it certainly feels like there are that many people. More and more trickle in throughout the day, changing the pace of how you move around and interact with the festival.  

Maybe I was just young and naïve my first year of Lollapalooza, but I can confidently say it didn’t feel as crammed and overwhelming then as it does now. Thank goodness I don’t care about getting in the front row most of the time because it would never happen for me with these crowd sizes. Like, I can’t even see the stage—I’m at this festival to hear and watch live music, and I’m forced watch it from large screens on the side of the stage.  

I typically stand farther back, especially for headliners, who most of the time I’m not super jazzed about. As I walked toward the Bud Light Stage to see Hozier close out the first day, I quickly realized I would not have many options. The crowd was backed up all the way to the street, thousands of feet away. It’s a doomful foreshadowing of what I’ll be faced with on Sunday evening, when I plan to actually see Blink-182 in the flesh on stage.  

Sets to catch on Day 2 

• The Stews (12:15 p.m. on Tito’s Handmade Vodka Stage) 
• Geese (1:45 p.m. on Tito’s Handmade Vodka Stage) 
• Wilderado (2:45 p.m. on Bud Light Stage) 
• Blu DeTiger (2:50 p.m. on Bacardí Stage) 
• RAYE (3:45 p.m. on Tito’s Handmade Vodka Stage) 
• Tiny Habits (4:30 p.m. on BMI Stage)  
• The National Parks (5:40 p.m. on BMI Stage)  
• Faye Webster (5:45 p.m. on Tito’s Handmade Vodka Stage) 
• Laufey (6:45 p.m. on Bud Light)  
• Megan Moroney (7:45 p.m. on Bacardí Stage) 
• SZA (8:45 p.m. on T-Mobile Stage) 

Kendall Polidori is The Rockhound, Luckbox’s resident rock critic. Follow her reviews on Instagram and X @rockhoundlb, TikTok @rockhoundkp