Country Star Brett Eldredge Talks Travel Habits, Must-Visit Chicago Spots, and Latest Music Drop

Country music mainstay Brett Eldredge isn’t slowing down. As fans return to live shows and travel rebounds, the multi-Platinum singer-songwriter, producer, and entertainer is moving forward, both creatively and geographically.

He’s flying more, writing more, and, most recently, releasing new music that sets the tone for a fresh chapter in his career.

The Must-Haves in Brett Eldredge’s Carry-On

Flying isn’t just a necessity for Brett Eldredge, it’s part of his creative process.

“I’ve written up a lot of scripts and treatments for my music videos on plenty of Southwest flights,” he told Travel + Leisure. “I don’t know why, I’ve thought up a lot of my ideas on planes.”

As a seasoned traveler, Brett Eldredge sticks to a few reliable essentials: a pen and pad for ideas, Bose noise-canceling headphones, and Oxigen water to stay hydrated. He also prefers audiobooks over traditional reading.

“I’m an audiobook listener because I’m dyslexic, so I can read fine, but I have trouble putting it all together. Since I’m an audio learner, I’m big into having headphones and listening to books on the fly.”

The ability to disconnect and think freely mid-air has become a kind of sanctuary.

Why He Loves the Skies And the Miles

Though he’s spent years touring coast-to-coast, Brett Eldredge still finds magic in flying. “It’s a wild feeling… my mind opens up out there.”

One perk that keeps him coming back? Southwest’s Rapid Rewards program. “I love racking up the miles,” he says. “It’s cool to be rewarded for travel, even when I’m not touring, I’m hopping on a plane.”

His go-to credit card lets him do just that. Add in Southwest’s flexibility with guitars, and the partnership seems tailor-made for the artist.

Lonestar Lovers Kicks Off a New Era

As he racked up more miles, Brett Eldredge also expanded his discography. He recently released two new singles, “You’ll Be Mine” and “Gorgeous,” from his EP Lonestar Lovers, which dropped on March 14 via his own label, Warm and Cozy Records.

The new tracks ushered in what felt like a bold, refreshed era for the artist.

This EP followed Merry Christmas (Welcome to the Family), his eighth full-length LP and third holiday album. His annual Glow Tour had become a seasonal tradition, supported by earlier holiday releases, Glow (2016) and Mr. Christmas (2021). His duet of “Baby, It’s Cold Outside” with Meghan Trainor remained a fan favorite, surpassing 207 million Spotify streams.

Lonestar Lovers shifted the mood from festive classics to modern love songs, with crisp production and the lyrical warmth that fans had come to expect.

Songs for the Open Road

Brett Eldredge doesn’t just write songs; he curates moments, too. His recent tracks make strong candidates for a cross-country playlist.

“‘Magnolia’ is a really good road trip song. It’s a feel-good song, and I think that would be great,” he said. “‘Gabrielle’ is a solid driving song. ‘Fall for Me,’ I would say, is a good one, too. They all have a rolling sound.”

For fans chasing summer freedom and open highways, his discography delivers a strong soundtrack.

Chicago’s Energy and Icons

Despite his national fame, one city continues to ground Brett Eldredge: Chicago.

“Portillo’s is a classic staple for Chicago food,” he shared. But for him, the city’s charm goes far beyond cuisine.

“Lake Shore Drive is a magic spot for me,” he explained. “You have the city, but also Lake Michigan right there with the waves crashing. People are out and about swimming… playing chess and checkers on the side. It’s a very great city feel, and one of my favorite happy spots in the world.”

Other favorites include Lincoln Park, the Lincoln Park Zoo, and Wrigley Field. “Those are some of my favorite spots,” he said.

Originally, his collaboration with Chase and Southwest Airlines for their Soundcheck concert series was planned for the iconic Chicago Theatre. The event pivoted to a digital format during pandemic restrictions but kept the personal fan interaction intact via one-on-one video sessions.

For many fans, it was a rare, intimate upgrade.

Closing Words

As for where he’s headed next? Brett Eldredge has his sights on Costa Rica. Hiking. The beach. Solitude in the forest. It’s not just a vacation, it’s the next place to refill the creative well.

Even in an era of streaming, social media, and short attention spans, Brett Eldredge gives out a different kind of message: Travel slow. Write often. Listen to yourself. And sometimes, the best way to move forward is to unplug and fly, headphones on, playlist ready.