By Dan Garcia Photographer Published Aug 06, 2024 at 7:01 AM

Lollapalooza was a musical paradise this year, offering a diverse lineup of artists and unforgettable performances at Chicago’s Grant Park. For music lovers in Milwaukee, making the trip to Chicago was a no-brainer, as the festival delivered a multitude of on-stage reasons to be part of this iconic event. With a lineup that spanned genres and showcased both legendary acts and rising stars, Lollapalooza 2024 was an experience that exceeded all expectations. 

Making the trip from Milwaukee was especially worthwhile this year, thanks to a variety of standout performances that captivated the crowds. From Megan Moroney’s soulful country set to Chappell Roan’s viral performance, Lollapalooza 2024 highlighted the incredible range of musical talent on offer. Fans were treated to memorable moments like Renee Rapp’s surprise collaboration with Chance The Rapper and Kesha’s always entertaining antics, making every minute spent at the festival an absolute delight. 

As we reflect on the incredible weekend, it’s clear that Lollapalooza 2024 was packed with reasons why music lovers should have made the 90-minute drive down I-94. Here are 20 standout moments that made this year’s festival an unmissable event. 

1. Blink-182 previews this week’s Fiserv performance 

Blink-182X

Blink-182’s Lollapalooza set was just a preview of the show they’ll deliver at Fiserv Forum on Wednesday. For those attending both, you certainly will have a week that you’ll remember forever. 

2. Megan Moroney put country music on her back for Lollapalooza 

Megan MoroneyX

With few country acts on the lineup this year, Megan Moroney’s standout Lollapalooza performance was a beacon for country music fans, making her set one of the festival's most memorable moments for country enthusiasts at the Chicago extravaganza in 2024. 

3. Benson Boone went from performing a ballad to doing a backflip all in the first five minutes 

Benson BooneX

Known for his hit single "Beautiful Things," Benson Boone – who opened for Imagine Dragons at Summerfest last year – showed why he’s a rising star with his captivating Thursday performance. From starting his set on the keyboard, to shifting into a high energy track where he backflipped between verses, Boone proved that he can do it all. 

4. Teddy Swims showed off his sense of humor 

Teddy SwimsX

Decked in his #69 Chicago Bulls jersey, the "Lose Control" hitmaker charmed the crowd with his humor and unique blend of R&B and country, proving his versatility as an artist and entertainer. 

5. Kevin Abstract proved his solo prowess 

Kevin AbstractX

Post-Brockhampton, Kevin Abstract demonstrated his individual talent, captivating Lollapalooza attendees with a powerful solo performance. Brockhampton who? 

6. Renee Rapp brought out Chance The Rapper 

Renee RappX

Her character Regina George may be a “Mean Girl,” but singer Renee Rapp was far from cruel to fans over the weekend. Rapp delighted her followers by bringing out hometown hero Chance The Rapper for a surprise collaboration that lit up the stage. 

7. Chappell Roan’s come up, fit for a feature film 

Chappell RoanX

Chappell Roan's journey from being dropped by Atlantic Records just a few years ago, even forcing her to take a job as a barista, to commanding the biggest crowd at Lollapalooza in recent memory with summer anthems like “Hot To Go!” and "Pink Pony Club" is a testament to her resilience and talent. Roan is living proof to continue following your dreams. 

8. Killer Mike delivered for OG rap fans 

Killer MikeX

With a set that resonated deeply with longtime rap aficionados, Killer Mike’s Lolla performance was a heartfelt tribute to the genre’s golden era. 

9. RAYE: the only Brit we can root for this month 

RAYEX

While we Americans probably aren't supporting any Brits during the Olympics, British singer RAYE’s breathtaking performance on Friday reminded everyone that music transcends borders and rivalries. 

10. Huddy proved he's more than a TikTok star 

HuddyX

Huddy’s Sunday performance on the BMI stage showcased his talent beyond his TikTok fame, earning him respect from the crowd as a legitimate artist. 

11. Tyla kicked off the festival with energy 

TylaX

Tyla’s early Thursday set was the perfect energizing start to the festival, with her dynamic performance setting a high bar for the weekend. 

12. "Greedy" for greatness 

Tate McRaeX

Tate McRae’s Saturday night set was so compelling that many fans chose to leave the festival – or at least just the stage – rather than stay for the stage’s headliners, Future and Metro Boomin, showcasing her magnetic appeal. 

13. Surfing at the Waterparks 

WaterparksX

Making their Lollapalooza debut, Waterparks had the crowd surfing like never before, creating one of the most high-energy moments of the festival. 

14. Kesha’s party-starting antics 

KeshaX

Kesha started her set by chugging a Pabst Blue Ribbon, setting the tone for a wild and unforgettable performance that was pure fun and more of a party than a pop concert. 

15. Two Door Cinema Club’s indie pop excellence 

Two Door Cinema ClubX

Two Door Cinema Club’s Sunday set was a perfect prelude to Blink-182, with their catchy indie pop songs getting the crowd ready for the night’s headliner. 

16. Victoria Monet paid dues to the legends before her 

Victoria MonetX

Victoria Monet seamlessly wove elements of classic R&B and hip-hop into her performance, paying homage to legends like Outkast and Beyoncé, adding a bit of nostalgia to her live performance. 

17. The Olivia Rodrigo Universe’s most underrated artist 

Conan GrayX

A key figure in Olivia Rodrigo’s circle, Conan Gray delivered a set that underscored his own star power, closing out the festival on a high note. As names associated with Rodrigo – like Chappell Roan and Gracie Abrams – have blown up in the past couple years, the pop star's close friend may just be the most underrated of the bunch. 

18. Hozier’s soothing contrast 

HozierX

Hozier’s soothing voice provided a peaceful counterpoint to Megan Thee Stallion’s high-energy performance, offering a whole range of experience for Thursday’s attendees. 

19. Future and Metro Boomin’s short-lived set 

Future and Metro BoominX

Despite technical issues and a disappointing curfew cut-off, Future and Metro Boomin’s set was a powerful demonstration of their collaborative genius ... although very short-lived. 

20. Chappell Roan’s record-breaking crowd 

Chappell RoanX

With an unprecedented 80,000-strong crowd singing along to every word, Chappell Roan’s Thursday set was nothing short of historic, solidifying her status as a breakout star of 2024. Her Lolla set was her biggest performance yet and will certainly be a notable chapter in her current rise to stardom. Need more evidence of her Lolla dominance? Blink-182 decided to close out Lollapalooza 2024 with a Chappell Roan cover.