Alexandra Kay Shines During Sold-Out House of Blues Chicago Concert
“This is the coolest room I think I’ve ever played,” she marveled.

Alexandra Kay Performs in Chicago, IL; Photo by Stephanie Siau
Hours before Alexandra Kay was set to take the stage for her debut in Chicago, IL’s iconic venue, House of Blues, fans lined up down the street in their best pink ensembles with glitter, bows and more, excited for the chance to see their favorite rising country star in action.
The Illinois native was proud to return to her home state this weekend to honor her journey as a former independent artist who recently signed a record deal with BBR Music Group/BMG Nashville. Over the past six years, she and her small team have worked tirelessly to grow her name and captivate fans with her unparalleled storytelling. The result of that hard work came through clear as day during her stop in the Windy City as part of her Cupid’s A Cowgirl Tour.

It’s not every day you see an artist at Kay’s level pack out a venue with a capacity of up to 1,800 people, but she pulled it off with ease. Even more impressive, her audience, which spans generations from young children to adult country music lovers, all united to sing along to nearly every song on her setlist.
“This is the coolest room I think I’ve ever played. This is so cool. It’s like every time I look up, I just see new people,” she stated to the crowd, while waving to fans down below as well as her family and friends seated in the upper level. “I can’t believe we sold out the House of Blues Chicago. That’s crazy. Thank you so much. It was a dream for me to play this venue. Never did I think the first time we got to play it that you guys would sell it out. Thank you so much.”

Starting the Night Off Strong With ‘Cupid’s A Cowgirl’
Kay kicked off the unforgettable 90-minute set with her latest release, a sassy female empowerment anthem titled “Cupid’s A Cowgirl.” Her positive energy radiated throughout the smoke-filled stage and soft pink lighting that illuminated her look featuring a pink feather-trimmed top, denim shorts with studded hearts embellishments, and dazzling silver cowboy boots.
The show continued with a few fan-favorites like “Backroad Therapy,” “More Than You,” “That’s What Love Is,” “Skip This Part” and her friendship anthem, “She Stayed.” Kay then took a moment to speak to her fans, letting them know that the night ahead would include several new and unreleased songs off her next album, but before diving into those, she wanted to celebrate the chapter that inspired her previous album, All I’ve Ever Known.
This 2023 collection offers a detailed diary of her divorce from a partner she was with for over a decade. As she learned to navigate all the trials and tribulations she went through during that time, there was one constant light guiding her out of the darkness – her fans. It was these listeners that stuck by Kay through what she calls “the hardest year of my entire life.”

“You supported me through writing this album and then putting this album out and my divorce being so public and my life being so public. In the middle of processing, it all, I got to meet a bunch of you guys every night and you guys would hug me, wrap your arms around me, tell me your stories. And I felt so much less alone,” she admitted. “And I just want to say more than anything, just thank you for that. Thank you for being there for me when I really, really needed you guys. And I just promise to always be there for you, even if that’s through my music.”
She went on to promise to continue to write songs that reflect her most honest emotions, just like she did in the project’s title track, which was the next song to unite the crowd in a massive sing-along full of healing and encouragement for the days ahead.
Setting The Tone For A New Project With Unreleased Songs
One of the most remarkable aspects of Alexandra Kay’s career is the way her fans know every word to every songs, even the unreleased ones. So when it came time to debut a few fresh songs like “The Last” and “Tomorrow Problems,” it felt as if they had been in her catalog for years. These songs are just a small look into Kay’s new record, that has found her writing from a much different place than her last album.
“It’s been really cool writing from such a secure, confident, purely joyful place,” she told the audience. “Since I was 12 years old when I started writing songs, I always wrote because I had really bad feelings and now I write songs because I am overwhelmed with happy feelings.”

Stand-Out Moments
In between hearing her signature vocals roar throughout the venue, Kay stopped the show several times to touch base with her fans. At one point, she paused to sign merch, speak directly to her fans and even make sure an emergency in the audience was handled properly.
Another memorable moment involved getting to help announce the gender of her bandmate’s first baby. She welcomed him and his wife to the front of the stage and erupted in screams of joy alongside the audience as bright pink lights shined down on them, indicating that a baby girl was on the way.
“I knew it,” Kay yelled enthusiastically before joking, “Too much pink in this camp not to be a girl. I knew it.”

For the second half of the show, Kay mixed things up with a vibrant cover of Chappell Roan’s “Pink Pony Club” as well as her collaboration with Julia Cole, “Best Worst Ex,” both of which ignited the crowd with their infectious energy before slowing down with a deeply personal moment.
Proving she is in her happiest lover girl era, Kay moved over to the piano where her boyfriend and bandmate, Rocko Beall began playing the delicate intro to “Second Wind.” The couple’s undeniable chemistry filled the room as she poured her heart into the lyrics, painting a picture of the newfound joy she feels over getting a second chance at love. Her raw emotion was even more palpable as she seamlessly intertwined a few lines from Elvis Presley’s classic, “Can’t Help Falling In Love.”
Showering Fans In Some Well-Deserved Gratitude
The songstress giggled with pure excitement as she made her way back to the center of the stage and took yet another opportunity to acknowledge all the support she felt in the room that night, thanks to all her fans who continue to show up for her.
“I want to also just say thank you guys so much for everything you did to me. You’ve been supporting me for so many years, before my album even came out, you guys found this random girl making coffee and singing country songs. And when the rest of the industry, it felt like, didn’t believe in me, you guys believed in me,” she gushed.

“So I just want to say thank you for completely changing my life. You guys put me on tour as an independent artist with Tim McGraw, you guys put me on tour with Jelly Roll…I was independent when all of those things happened, and the only reason anybody paid attention is because you guys made them pay attention. You blew up my videos, you blew up my music, you streamed my songs so many times. So everything that I have, this sold out House Blues Chicago is because of you. So thank you from the bottom of my heart. I’m always going to give you guys the credit because I have none of it without you. So thank you.”
Kay delivered one more song alongside her tour mate, Logan Crosby, who she invited back to stage to help perform the powerful “How Do We Go.” The same infectious spirit and signature twangy vocals that Crosby opened the show with once again captivated listeners through the emotive breakup tune.
Closing The Show With A Two-Song Encore
Technically, the setlist had reached its end, but fans made it clear they weren’t going to let Kay leave Chicago without delivering two of her most beloved tracks. As soon as she stepped off stage, the venue erupted in cheers and the crowd began chanting her name, determined to bring her back. Their energy paid off.
Moments later, Kay made her grand return, standing in the center of a nine-foot, fully-lit heart structure, setting the perfect scene for her encore. The audience somehow found a way to get even louder as she closed the night with “Painted Him Perfect” and “Everleave.”
Between all the unforgettable moments, sing-alongs and conversations of the heart that unfolded during her Chicago concert, Alexandra Kay further proved that she doesn’t just put on a concert. Instead, she brings a celebration of love, pure country music, and the unwavering bond she shares with her fans.
While listeners await Alexandra Kay’s next project, they can find her lighting up stages throughout the remainder of her Cupid’s A Cowgirl Tour. Once this trek wraps up at the end of April, she will embark on a run of sold-out dates across Amsterdam, Glasgow, Birmingham, Belfast and Manchester for her international All I’ve Ever Known U.K. & Europe Tour. Then, Kay will join Brad Paisley on select dates of his Truck Still Works World Tour this summer.
A full list of upcoming tour dates can be found HERE.
Madeleine O’Connell graduated from North Central College with a bachelors degree in Journalism and Broadcast Communications before deciding to pursue her studies further at DePaul University. There, she earned her masters degree in Digital Communication & Media Arts. O’Connell served as a freelance writer for over two years while also interning with the Academy of Country Music, SiriusXM and Circle Media and assisting with Amazon Music’s Country Heat Weekly podcast. In addition to Country Now, she has been published in American Songwriter, Music Mayhem, and Holler.Country. Madeleine O’Connell is a member of the Country Music Association and the Academy of Country Music.