The Windy City is a city celebrated for its diverse offerings—from historic sports traditions and mouthwatering cuisine to stunning scenery and a vibrant arts and entertainment scene. And for the past 20 years, every summer the city has turned up the volume, welcoming music lovers from around the world as the Lollapalooza festival takes over Grant Park.
For four days straight, more than 460,000 festivalgoers immersed themselves in experiences designed to appeal to a wide range of audiences. From Doechii and Tyler, the Creator to A$AP Rocky, Sabrina Carpenter, and Olivia Rodrigo, the lineup served up sounds for every vibe and taste. As a first-time attendee, I was deeply moved to see so many different kinds of people come together, each creating their own unique experience within the same shared space.
Airbnb, a global partner of Lollapalooza, treated festivalgoers to their own experience, a unique escape with its exclusive on-site lounge, Airbnb Haven. Nestled toward the back of the festival grounds beneath the much-needed shade of tall trees, the space offered a serene retreat from the crowds. Inside, guests were greeted by a setup that evoked the charm of a treehouse, complete with wooden panels and lively touches like bright orange beanbags for lounging and green stools for seating.
They offered guests a handy shoe-cleaning service, an essential perk given that so many performances and activities took place on dusty, well-trodden grounds. Just steps away, the glam station buzzed with creativity, transforming attendees into festival showstoppers—braids woven with bursts of colorful hair pieces, faces shimmering with rhinestones and jewels, and makeup looks as bold and vibrant as the music itself.
Not only was Airbnb focused on providing accommodations— they also rolled out a variety of sign-up experiences, ranging from photography tutorials and makeup sessions to personal styling and DJ lessons.
Since we were in the birthplace of House music, it was only fitting that Chicago’s Queen of House, DJ Lady D, hosted her own experience: Learn How to Mix with DJ Lady D at Lollapalooza. A true Chi-town native, she’s been attending the festival for over 15 years. After two years of performing as a guest, she achieved her dream of playing a solo set in 2010, and the following year made history as the first woman to perform on the Perry Stage—the festival’s epicenter for EDM—which, this year, was headlined by Chance the Rapper.
In a full-circle moment, she returned to the very festival she once dreamed of playing—this time sharing her passion by teaching others the craft she loves.
“The fact that they [festival attendees] want to take an hour out of their day at Lollapalooza and spend it with me is something I’m super grateful for,” DJ Lady D told ESSENCE.
In a secluded corner of the Airbnb activation location, guests stepped into a silent disco party hosted by DJ Lady D herself. After meeting her and receiving a crash course on working a DJ system like a pro, they were handed headphones, through which DJ Lady D’s voice guided them through the basics of navigating a Pioneer DJ System.
She kicked things off with the funky old-school classic rhythm of “The Percolator” to energize the crowd. Then, she demonstrated how to layer different beats and notes. One by one, guests had the chance to take the stage and create their own mixes alongside the Queen of Chicago House music.
As someone who would be considered a younger festivalgoer and newly introduced to House music, I resonated with not only her lesson but DJ Lady D’s advice: “I hope young festivalgoers get the whole experience in its totality,” she says. “I think you should venture out and explore all the different types of music and experiences available, and just open yourself up to everything it can be.”
DJ Lady D wasn’t the only woman sharing her expertise at Airbnb Haven. For festivalgoers eager to tap into their inner fashionista, a major highlight was Curate Your Lollapalooza Fit with Ann-Marie Hoang, a fashion experience led by the veteran industry stylist herself.
Hoang is an award-winning stylist and designer whose portfolio spans a roster of A-list clients. She has crafted looks for Beyoncé and Rihanna’s NFL halftime performances and styled music video wardrobes for artists such as Megan Thee Stallion and Drake.
Growing up on the East Coast has greatly shaped Hoang’s fashion influences over the years.
Hoang told ESSENCE that life in Los Angeles offers inspiration from every direction. Which she uses to her advantage when it comes to styling others.
“Instead of putting everyone in a specific category, I like to mix it all up and try to create something new,” said Hoang.
While preparing for her experience, Hoang aimed to ensure it would be enjoyable for all attendees. “It was fun to research all the different trends happening right now and try to make it work for everyone,” she says. “I wanted a little something for the guys, the girls, the gays—colorful pieces, masculine styles, silver, gold. It was literally a treasure trove.”
And she delivered exactly that. From bold, furry hats in vibrant colors to edgy, spiked belts, it was clear Hoang had thought of every possible look. Guests began the experience with their “original canvas”—the outfit they arrived in—then explored the space to pick out pieces and accessories to transform their festival fits. There was even a charm bar for creating custom jewelry, all while receiving personal styling tips from Hoang herself. To capture the magic, before-and-after photos were taken, showcasing each guest’s style evolution.
Guests strutted out grinning ear to ear in their newly styled fits — but the good vibes didn’t stop there. The stylist herself picked up a few fresh tips and tricks from the crowd, proving it was a style swap for everyone.
“”That’s what I love to see — everyone’s interpretation of how to wear a piece. And that’s just me being open-minded. I learned something from everybody today,” Hoang said.
The experiences provided by Airbnb showed that beyond the stages and headliners, Lollapalooza offered moments of discovery, self-expression, and community. It became a space where people from all walks of life could come together, feel seen, and know they belong — no matter who they are or where they come from.