Chicago can’t get enough of rising country sensation Ashley Cooke. On Friday, Feb. 14, she made her highly anticipated return to the Windy City and once again filled the iconic Joe’s on Weed St. to capacity, with many fans coming back for another unforgettable night.
“Chicago has some diehard fans, so it’s really fun to get to be here. And last tour when we did Joe’s, it was one of my favorite shows on the whole tour. So it’s fun. It’s going to be a really good night. I’m excited,” Cooke shared with Country Now prior to taking the stage.
While the venue is known for its intimate setting, Cooke managed to make it feel like an arena-sized experience as she ignited a full-blown singalong right from the start.
“It is damn good to be back in Chicago, IL,” she shouted upon making her grand entrence, wearing a stylish denim cheetah print set.

The Florida native kicked off her nearly 90-minute show with an electrifying delivery of “Getting Into” before leaning into her collection of personal breakup anthems with songs like “Good To Be Back,” “Moving On With Grace,” “I Almost Do” and “Already Drank That Beer.”
Couple Gets Engaged During “Never Til Now”
While Cooke has her fair share of pain-filled relationship tunes, she also knows how to shine with tracks that highlight the better sides to love. With the show falling on Valentine’s Day, she made sure to highlight the couples in the crowd by dedicating her performance of “Never Til Now” to them.
As she sang, couples embraced, swaying back and forth to the melody, and in a truly unforgettable moment, one pair even got engaged. Cooke made sure to call out and acknowledge how special it was to see such a monumental memory being made at her show.
“It’s your eighth time seeing us and you just got engaged?” Cooke said into the mic while taking the time to speak with the newly engaged couple. “I am going to see you guys after the show. You guys, congratulations. Seriously, huge. Congratulations. Oh my God, you guys, that’s so special on Valentine’s Day.”
Continuing with the theme of love and happiness, she showcased a new song that has been gaining fans approval through social media, meaning many in attendance already knew the words to “Baby Blues.” She revealed that this song marked a look into her sophomore album that has been keeping her busy in the studio. “more on that soon,” she teased.
@countrynow.com @Ashley Cooke teases new album with unreleased track, “Baby Blues.” 👀💙 #countrymusic #babyblues #ashleycooke #chicago ♬ original sound – CountryNow.com
Slowing Things Down And Reflecting
Between love, heartbreak and all the other ups and downs that have inspired her music, fans have been with Cooke through it all. So it only made sense to take a moment to slow things down and have an honest reflection with the audience using just her voice and an acoustic guitar. She first dove into one of the first songs she ever posted on social media – Morgan Wallen’s “Chasin’ You.”
“Need to break it back down just to acoustic guitar and you guys. This is how this whole thing started. So we’re going to do a few songs just like this, if that’s okay with you guys,” she shared before plucking her guitar to the hit tune.

Overcoming A Difficult Year
Next, Cooke opened up about the struggle of a year she had. Silence washed over the audience as she spilled her heart out about a recent breakup, her battle with family loss and learning of her dad’s cancer diagnosis. This led to the debut of another new song titled “Getting Old” as well as her brutally candid song, “It’s Been A Year,” both of which definitely had fans in their feels as it allowed them to reflect on the hardship in their own lives.
“Last year was a really tough year for me,” shew admitted. “I lost both of my grandmas in the same year and I went through a breakup with my boyfriend of two years and my dad got diagnosed with cancer and it sounds a good damn country song. I guess it is one. Honestly, I got to the point that I was so exhausted that I almost wanted to stop creating, which is so not me.”
Cooke continued to reflect on the difficult chapter and how she learned to overcome it. “I had kind of a come to Jesus where I said, if I’m going to keep doing this, getting up on these stages and playing music night after night, I want to say something that I really mean and be honest about exactly where I’m at in my life. And I started the year off in a cabin in Alabama with some of my best friends that are amazing songwriters, writing songs about this past year and what it all meant to me. And over a bottle of wine and a lot of honest conversations. We wrote this next song, it’s called ‘Getting Old.’”
Amping Up The Crowd With Country Classics & A Special Guest

She brought the energy back up by inviting her band back to the stage and surprising fans with a special addition to the setlist as a thank-you for yet another sold-out Chicago show.
This electrifying portion of the show featured a string of classic country hits that always gets a crowd singing along – Gretchen Wilson’s “Redneck Woman,” Shania Twain’s “Any Man Of Mine” and Carrie Underwood’s “Before He Cheats.”
As the night neared its end, Cooke invited opener Greylan James back on stage to perform her duet originally recorded with Nate Smith, “See You Around,” followed by “Back in the Saddle.”
For the grand finale, she delivered the song that inspired the name of her headlining tour and earned her first-ever No. 1 hit, “Your Place.”
“It’s your place tonight, Chicago. Thank you for buying a ticket, for supporting my music, for being here tonight. I could not love y’all more. We will see you next time. Get home safe, I love you so much,” she said with nothing but truth and sincerity in her voice upon waving goodbye.
In Her Confident Era

At this point in her career, Cooke has reached a new level of confidence that allows her to focus on having more fun and worrying less about trying to prove herself on stage. She admits that being on the road felt “way different” last year compared to her current run and now, she is in love with this new era of being “a lot more settled.” This mental shift is evident from the audiences perspective too, as she fills the room with a vibrant energy.
“I get to actually truly enjoy the moments more this time around than I think I realized I wasn’t doing last time,” she admitted.
This unforgettable Chi-town concert marked another stop on Ashley Cooke’s headlining Your Place Tour. The trek kicked off last October and picked back up in January. She and special guest Greylan James will continue hitting cities across Tennessee, New York, Massachusetts and more through March.
The post Ashley Cooke Takes Chicago by Storm With a Sold-Out, Unforgettable Show appeared first on Country Now.