I won’t lie, over the course of the past year or so, I’ve talked to Alexa less and less. While the Amazon Echo Dot ($50) sits on my countertop right next to my desk, the most I’ve asked of Alexa is the daily weather report, instead opting to stream Spotify on my browser or have Chat GPT put together the impromptu recipe for dinner. But when the Amazon team invited me to Chicago’s Lollapalooza music festival, where they were hosting an interactive activation to promote the launch of Alexa+ ($20/month or free for Amazon Prime users) – the newest generation of Alexa powered by generative AI – it changed everything.
I’d been to Coachella and Governors Ball, but Lollapalooza would be a new experience in itself for me, where I was looking forward to seeing artists like Doechii, Rüfüs Du Sol, and Sabrina Carpenter. Only, outside of enjoying the concerts, I had no idea how many miles the grounds spanned, where to eat, what to wear, and what to see in the surrounding Chicago area. Luckily, Alexa+ helped with all of that.
While the model is currently in an early access stage, rolling out slowly to Amazon device owners, I got to preview the highly capable tech and was amazed by her capabilities as she helped me pack and plan for my weekend from start to finish. In the process, she sort of became my BFF – because this version of Alexa actually gets to know you, from your likes and dislikes to your favorite cuisine, music preferences, and even unspoken habits (yes, really).
Ahead, I share how Alexa+ supported me personally on my first-ever trip to Lollapalooza.
What to Wear to Lollapalooza
Ahead of my trip to Lollapalooza, I was sent the Amazon Echo Show 15 ($300) to test out Alexa+. I set up the 15.6-inch hub on my living room coffee table and got to chatting as I planned my outfits. As I constructed boho-leaning ensembles, I asked Alexa+ to remind me of the festival lineup each day so I was able to establish a vibe based on the artists I was seeing, and I had her streaming their music in the background while I constructed each look. She was also able to instantly inform me of the bag requirements when I asked (clear bags must be 12″ x 6″ 12″, whereas fanny packs and mini bags must be 6″ x 9″ or smaller) – which is exactly how I knew that packing my Brandon Blackwood Denim Shoulder Bag ($179, originally $255) would be a safe bet after grabbing my measuring tape. I mean, how handy?!
My foolproof Lollapalooza essentials, as recommended by Alexa+, were my Los Angeles Apparel Denim Loose Cuff Shorts ($72); Maui Jim Noni Polarized Sunglasses ($429); Thursday Boots – shop similar: Tecovas The Annie ($365); and Zara crochet pieces, from the Zara TRF Mid-Rise Wide Leg Scarf Jeans ($70) to the Zara Pointelle Knit Top ($46).
What to Do in Chicago Near Lollapalooza
When I arrived at the Palmer House hotel in Downtown Chicago the next day, an Amazon Echo Show 8 ($150) was waiting in the room so that I could log in and continue my conversation with Alexa+. During the trip, she kept me on time by telling me exactly how long it would take to Uber to Tanta Chicago to meet the rest of the Amazon Alexa party for dinner, and sharing walking directions to brunch at Cindy’s Rooftop on day two (get the monkey bread! I’m still drooling). She also recommended a great spot for lunch in between sets right near the festival: Remington’s, where I enjoyed the most delicious black cherry margarita and the best filet sliders of my life.
After spending the full weekend at Lollapalooza with Alexa+, I really think my favorite element is her ability to multitask. She was able to stream festival music while walking me through my daily agenda and directing me to Chicago hot spots – and that’s only continued since I’ve returned home. For example, last night I streamed my favorite Netflix show while Alexa+ walked me through a recipe step by step verbally – and I didn’t even have to stop and look down at directions.
Sarah Wasilak (she/her) is the PS Shopping Director. With plenty of experience in the fashion industry and over 11 years as an editor at the brand, she enjoys writing and creating social videos across the lifestyle, health, and fitness categories. She is the host of the “Dinner for Shoes” podcast and has bylines at InStyle, Elle, Refinery29, Who What Wear, Elite Daily, Byrdie, and The Quality Edit.
Travel and expenses for the author were provided by Amazon Alexa for the purpose of writing this story.
