Lollapalooza Leveled Up for 2026: Everything We Loved About the Festival This Year

Festival season is coming to a close, with Lollapalooza one of the seasonal indicators of the final drag of the dog days. The four-day Chicago fest goes down in late-July/early-August every year, taking over Grant Park for one of North America’s most anticipated annual music events. Right in line with April’s Coachella and June’s Bonnaroo, Lolla stands out in that it’s one of the only festivals to still stretch four full days. However, Lollapalooza’s 2026 iteration saw the Chi-town fest offer up one of its most impressive years, giving Coachella a real run for its money.

For starters, this year’s curation of talent was a four-day force to be reckoned with. Headlined by the Mount Rushmore of Pop Girlies – Lorde, Charli XCX, Olivia Dean, JENNIE, and Tate McRae – the leaders of the lineup all graced Grant Park at particularly important times.

Fresh off her first post-brat release, Charli XCX arrived in Chi-town ready to live debut new album Music Fashion Film. For Lorde, this marks her first-ever time headlining the coveted festival, after her set got cancelled due to weather after four songs when she first played Lolla 12 years ago. On the heels of one of the most impressive banner years, Olivia Dean’s Lolla headlining set signals her first-ever headlining slot at a US festival. JENNIE and Tate McRae are both deep in album rollout mode, with all eyes on the K-pop star as she made history on the stage as the first solo K-POP headlining act, and Canada’s pop princess as she continues to not-so-subtly tease her new project. Other notable pop names included Slayyyter, MUNA, Zara Larsson, ADÉLA, and beabadoobee.

Lil Uzi Vert – before their set was canned – was a good get, too, the rapper gearing up for some sort of longform release. Little Simz was another we were especially excited about, the UK rapper actually ending up running a last-minute surprise DJ set at Hacienda PATRÓN; the rare, intimate set in the middle of Grant Park is closest many will ever get to Simz. Dev Hynes made a stop in Chi for Lolla amid his busy summer run of shows, while Leon Thomas slid through on his birthday (and brought Babychiefdoit).

Along with the A-listers, emerging talent from across the globe are also platformed both on and off the official lineup. New York five-man-unit WHATMORE brought its undeniable NYC ethos to the Midwest, while Love Spells, Wolf Alice, Ecca Vandal all nabbed spots on the calendar. At Hacienda PATRÓN, a selection of local Chicago DJs took the decks to spin vinyl all weekend.

It goes beyond the music, of course, with a slew of brands, activations, and local eateries popping up throughout the festival grounds – which, truly unlike any other festival, goes down smack dab in the middle of the city. What that means, though, is arguably the best part of the entire affair: everything you see is backed by the full Chicago skyline.

At Lollapalooza, every single artist brought their A-game, making the 2026 festival a strong contender in the running for the best of the year. From the custom high-fashion looks to the on-stage collaborations and standout sets, we’ve rounded up everything we loved about Lollapalooza 2026 below.

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Little Simz Goes B2B: Stage Performance to DJ Set

Leave it to Little Simz to make two festival performances in one day look like light work. The newest Miu Miu ambassador has been on a crazy run this summer, alternating between routine tour stops and festival performances including Barcelona’s Primavera and Montreal’s Osheaga. Lollapalooza marked the first stateside stop on her summer escapade, and she did it big. On Thursday, Simz first led one of the most captivating, high-energy sets of the entire four-day-stint before announcing a surprise DJ set at Hacienda PATRÓN. For an intimate crowd in the immersive PATRÓN x Live Nation activation, Simz spun vinyl and showcased her range, which knows no bounds, mixing Keinemusik in with Drake and Central Cee. Two totally different energies, one true multihyphenate artist.

Destin Conrad Dons Custom Advisry

One thing about Destin Conrad? He (with the help of his trusted stylist X) is guaranteed to flex on the entire audience with his on-stage fit. Conrad is a known supporter of Keith Herron‘s Advisry, most recently wearing a full custom look by the brand to the BET Awards. Conrad ran it back with Advisry once again in another custom outfit. The all-red look included a flowy red button-down shirt and gingham shorts, which he paired with a black and red loafer and red sock. Conrad told Live Nation that Jamaican styling has been a point of creative inspiration for X as of late, also lifting from Conrad’s current genre-bending as he gears up to release his reggae album later this month.

Blood Orange’s New Visuals: “Grief, Love, England, Youth and Music”

For Dev Hynes, even at a 4:45 pm festival set, a live performance is always one-of-one. Like his close friend Simz, Hynes finds himself on a big festival run this summer, with stops at Coachella, Governor’s Ball and Primavera before Lolla, and each of these sets has been completely different from the last. At Lolla, Hynes debuted a new slate of visuals rooted in two themes of “Grief, England, Youth and Music” and “Love, England, Youth and Music.” In the nostalgic new visual suite, Hynes intermingles archival soccer footage with film clips, music videos, and news segments as he played “Champagne Coast” and covered Björk.

Geese Follows Up Its Performance With Basketcase Merch Drop

“Thank you to United Airlines for losing our guitar,” Cameron Winter said at the opening of Geese‘s Saturday set after playing a rendition of “2122” mixed with some of Chicago’s “25 or 6 to 4.” “The buck stops at United tonight. The quality of the show is up in the air, so to speak.” The 11-song set was a highlight of Saturday, with drummer Max Bassin donning a yellow “Who the Fuck is Cameron Winter” shirt, designed by Basketcase for the band’s festival performance. The day after the festival, Basketcase released a full slate of Geese merch, including Bassin’s shirt.

Leon Thomas Brings Out Babychiefdoit During His Birthday Set

The definition of a duo we didn’t see on our bingo card. On Leon Thomas‘ birthday, he graced us with a hypnotic, seven-song Lollapalooza set complete with a very unexpected special guest. South Side Chicago native Babychiefdoit pulled up for a surprise performance of his current hit “Ghetto Love Story.” Never thought we’d hear that song in the same ten-minute span as “MUTT.”

At Hacienda PATRÓN, If You Want to Spin, You Have to Spin Vinyl

Patron’s Hacienda PATRÓN is also on a crazy festival run this summer. After appearances at Bottlerock and Austin City Limits, the immersive two-story space touched down at Lollapalooza. Inspired by the brand’s iconic distillery in Jalisco, Mexico, and includes multiple bars (Headliner Margaritas, Lolla Lemonades, and Palomapaloozas on tap) and a full DJ deck and stage area, where the only rule is that in order to spin, you’ve gotta spin vinyl. A lineup of local Chicago DJs slid in and out of the Hacienda all four days, with standout sets coming from Tommaso Conforti, Blesstonio, Jake Hopes, and Successful Twan. Local pop duo Haute and Freddy also delivered a live performance, and Little Simz pulled up for a surprise DJ set after her main performance.

beabadoobee’s Many Guitars (and Meme-y Merch)

With her fourth studio album Pylon on the horizon, beabadoobee is in full rockstar mode. As a prelude performance to her August-through-December headlining world tour, beabadoobee took the Lollapalooza main stage on Sunday before her first show of the run on August 4. For a setlist of both her early-career classics and new Pylon singles, beabadoobee alternated between a slew of different guitars, both electric and acoustic. She played on both bright pink and pastel blue electric guitars, as well as a dented deep red one. On the drumset, an edited image of beabadoobee and “I Love Pylon” are stamped on the bass drum, and beabadoobee herself donned a black tank top that read “Pylons Rule.” Masterful, memed-out self-promotion.

JENNIE Debuts Four New Songs During Her Headlining Set – in Custom Ann Demeulemeester

JENNIE made history the only way she knows how during her Lollapalooza Saturday night performance. The star took the stage as the first-ever Korean female solo artist to headline the festival, dripping head-to-toe in custom Ann Demeulemeester styled by Sam Woolf. After opening with the classics – “ZEN,” her “Dracula” remix, and “Mantra” included – and her most recent release, “Less Than a Lover,” JENNIE pivoted to a four-track run of unreleased cuts. First, she played the long-teased “Sweet Tooth,” followed by “Fallen Angel,” “Lock it Down,” and “Heaven.”

Lil Uzi Vert Makes Up For His Cancelled Performance With New EP, Surprise Appearance at Major Lazer

One of the only downsides of the festival came mid-day Friday, when the rain cancelled Lil Uzi Vert‘s set. Vert instead popped out for a few songs during Major Lazer‘s 9:00 p.m set, but unfortunately, we were at Charli so we missed it. The rapper continued their birthday tradition and dropped off new studio offering, Maverick: “Almost Forever” EP.

Slayyyter’s Homemade Fish-Filled Outfit

Drawing one of the biggest crowds for a non-headlining performance of the entire four-day run was our favorite WORST GIRL IN AMERICA, the pop anti-princess (?), Slayyyter. Just hours off her surprise new single “brand new chanel$,” Slayyyter showed out in a fisherman-inspired look, styled by Hunter Clem. The musician made the tackle-belt skirt herself, which she and Clem paired with a DSQUARED2 flannel corsetted top, Hunter rain boots, and a bedazzled fish clutch (and, at one point, a fishing rod, too).

Worlds Collide: Sombr Brings Out 5SOS for “She Looks So Perfect”

On Thursday night, Sombr‘s sunset set was the place to be. Continuing his series of standout live performances, the Grammy-nominated Best New Artist looked the part in an all-black look, spanning a feather-trimmed band jacket custom-made by Yarden Dachut and flare-leg pants by Haitch. Mid-set, Sombr brought out 5 Seconds of Summer right after the band’s set wrapped for a collaborative performance of “She Looks So Perfect.” The edgy pop-boy combination we didn’t know we needed.

Kwn Rocks Hometown Label House of Errors

Hailing from East London, kwn came a long way for her debut Lollapalooza set, and she did not disappoint – nor did she forget to pay tribute to where she came from. For her outfit of choice, kwn chose to rep London’s very own House of Errors, flexing one of our favorite sets from the brand: the Embroidered Moss Denim Jacket and Pants. The light-wash denim jacket and matching jeans are defined by all-over moss-like detailing throughout.

Clipse’s Comeback Tour Never Ends

One of the standout sets of the weekend, to no surprise, came from Clipse. Pusha T and Malice must not get tired, because despite the duo’s absolutely stacked return run – which began over a year ago now – it hasn’t halted once since the July 11, 2025 release of Let God Sort ‘Em Out. The latest in the unit’s comeback tour was a Saturday evening Lollapalooza set, and once again, we have no notes.

Lorde, in Issey Miyake, and Charli XCX Work It Out on the Main Stage

We got a true Eras Tour from Lorde on a Thursday night in Chicago, who stepped onto the Lollapalooza stage as the first headliner of the festival – also marking her first time headlining the festival after first performing back in 2014. Her set got cut short back then, so in a true full-circle moment, Lorde ran through all of the 2014 classics in addition to our Virgin favorites, and, of course, Charli XCX’s “Girl, so confusing” remix with Charli herself. Lorde donned a bright pink Issey Miyake hoodie, atop a bright pink bikini top. “The future looks a little bit different than I imagined,” she said to the crowd as the show started to wind down. “It’s harder and darker. I dream about fire all the time now, and I’m scared. But us meeting up and dancing and crying and singing to each other, that is one of the best ways I have to feel alive. I’m sorry to say it’s going to get harder and darker, but we can stay awake, we can stay alive . . . I want you to ask yourself every day, am I acting trapped or do I wish I could be acting free? … We gotta stay awake in this moment . . . it’s ours, and it’s beautiful.”

The TURNSTILE Pit

One of the festival’s final acts was TURNSTILE, on Sunday at 7:00 p.m. It took two songs before Brendan Yates jumped into the crowd, performing the third track, “ENDLESS,” from the audience. One of the only sets of the entire fest to have an encore, the official set ran 11 songs, with three more added at the end. Confidently, we can say this was the best pit of Lollapalooza, and we think Yates would agree.

Frost Children Bringing Out Lucy Bedroque After Their Set Was Cancelled

When the rain hit on Saturday, the original day’s lineup went out the window. While most of the acts got rescheduled, a handful of the early sets were canned altogether. While Frost Children was lucky enough to get rescheduled to a later set time, Lucy Bedroque was not, their set unfortunately getting cancelled. Luckily, after the duo wrapped its expansive, era-spannig 12-track set, they brought out Bedroque for a performance of “2010 Justin Bieber” to close the show. The night prior to their originally scheduled set, Bedroque performed an official Lollapalooza aftershow. Completely sold out, the intimate performance included a surprise appearance from Jane Remover.

Inji’s Bright Pink Bronco

Inji’s Lolla debut saw the Turkish, Philadelphia-based artist leave it all out on the stage – literally. Wearing a pink ruffled dress and a “Miss Bright Ideas” sash, the musician brought a full-size bed to the stage, as well as a bright pink mini Ford Bronco car.

Charli XCX’s Spectacle of a Music Fashion Film Live Debut

After a series of intimate pre-release shows and a one-off Nashville performance, Charli XCX’s Friday night Lollapalooza set marked the first time Music Fashion Film would be played live on a proper stage. Needless to say, all eyes were on Charli Friday night, who hit the stage just a week after releasing the post-brat opus. A perfectly crafted setlist included an assembling of the brat classics, early favorites (“Track 10”), the Wuthering Heights soundtrack, and Music Fashion Film in full. The rain kicked in at the perfect time, during House, as Charli set off fireworks from the stage. Something was definitely in the air, as the show – which many are saying is Charli’s best of her career – went down the night before her birthday. Music Fashion Film‘s formal introduction to the world showcased the record’s aesthetic down to the styling, with Charli swerving between a stripped-down series of leather sets, tattered tees, and vintage YSL. Despite rumblings, there weren’t any cameos. They weren’t needed anyway. Just Charli in her prime, fresh off her post-apocalyptic album, during Leo season. She closed out with David Cronenberg feature “No One Lasts Forever,” with the “Oblivion is freedom” lyric acting as the closing monochromatic visual. Now that is how you headline a festival.

Olivia Dean Draws a Crowd of Almost 100,000 For Her First Time Ever Headlining a US Festival

Pure joy was palpable on Saturday night as Olivia Dean closed out the third day of the festival with her debut headlining gig at a US festival. Sam Fender made an appearance for the pair’s chart-topping track, “Rein Me In.” The entire time, Dean was visibly floored, in tears of joy as she looked out into the sea of 97,000 attendees in her gold custom Versace gown. As she should.