Country Music Singer Brett Eldredge Shares His Favorite Airline Perk, Road Trip Music, and Must-visit Spots in Chicago

Brett Eldredge is officially back and better than ever. The country music sensation took some much-needed time away from the spotlight to perfect his latest album, Sunday Drive, which he released last month. He took a step back from everything, paused his life on the road, and even went as far as giving up his smartphone.

“I lost a little bit of the excitement of what I do. I got burnt out on the game of it all with nonstop touring, and going and going, and never taking time for myself,” he told Travel + Leisure. “So, I got a flip phone and a polaroid camera, and I started playing less shows. I wasn’t doing anything, except listening to who I wanted to be as an artist and that’s when I really started to shine through. I got on a deeper level with myself and my music and it was an amazing experience.”

Now, he’s ready to reconnect with his fans more than he ever has before. Keeping in mind the safety measures during the coronavirus pandemic, the star teamed up with Chase and Southwest Airlines for a digital version of Soundcheck. This is a beloved initiative put on by the two brands, which allows Southwest Rapid Rewards cardmembers to trade in their travel points for the ultimate VIP meet-and-greet concert package. Eldredge originally planned for Soundcheck to be held at the well-known Chicago Theatre, but due to COVID-19, he pivoted to including one-on-one time with the frequent fliers via video chat. For some lucky Eldredge enthusiasts, it was the dream upgrade from those daily work Zoom meetings.

In addition, Eldredge dropped an exclusive set of songs from his newest album on YouTube, which he filmed from a studio in Nashville. Ahead of the exciting affair, T+L chatted with Eldredge about all things Chicago and the destination he’s most looking forward to visiting next. Read about it below, and click here for future Rapid Rewards events that Southwest travelers can save and use their points on. There are already several digital happenings scheduled for the fall and spots are filling up fast.

T+L: First things first, when you were traveling, which items did you always have with you in your carry-on?

Brett Eldredge: “I’m a huge headphones guy, like the Bose headphones. The big ones because they’re noise-canceling, which is really great for me. 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.

I also journal sometimes on planes. I’ve written up a lot of scripts and treatments for my music videos on plenty of Southwest flights. I don’t know why — I’ve thought up a lot of my ideas on planes. I’ll get to free thinking on a flight because I have kind of a wondrous feeling when I’m flying. It’s still kind of a crazy thought that we can fly on a big bird in the sky. It’s a wild feeling. It’s so cool, so my mind opens up out there and I get creative.

I have a pen and pad, headphones, and stay hydrated and I’m good to go. I drink Oxigen water, which I love. The formula is really good and hydrating. I’m so active all the time. I’m usually hiking when I’m traveling, so staying hydrated is key and Oxigen is what I use a lot. I also have a Tumi suitcase.”

What’s your favorite airline perk?

“I think it’s always been when I use my Southwest Airlines credit card because I love racking up the miles. Usually, I’m flying all the time, and so, it’s a really great thing to know that when I’m spending money to travel, I’m also getting rewards. It’s cool to be rewarded to travel. I love going places. Even when I’m not touring, I’m hopping on a plane. They’re also cool about me carrying on my guitars and stuff.”

Congratulations again on your new album. Which tracks would you say make the perfect road trip music?

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

Since fans can’t be in Chicago for Soundcheck, what are some of your favorite places that people should make note of for future trips?

“Portillo’s is a classic staple for Chicago food. Also, Lake Shore Drive is a magic spot for me. I love the energy down there. You have the city, but also Lake Michigan right there with the waves crashing. People are out and about swimming, even if the water is really cold. People are also playing chess and checkers on the side. It’s a very great city feel, and one of my favorite happy spots in the world. I love Lincoln Park and the Lincoln Park Zoo, too. And, of course, Wrigley Field where the Cubs play. Those are some of my favorite spots.”

Have you been keeping up with the audience-free games?

“Yeah, I’m just glad to watch some kind of baseball. I would have been there for the opening game, you know? Well, if I wasn’t on the road. I love the nostalgia of baseball, so just the fact that they’re playing in some way is exciting for me, but it is strange for the players not having the crowd there. At least they’re able to play and we can watch from home.”

Lastly, where’s the one place you want to travel to next?

“I really want to go to Costa Rica. I love to hike, I love the beach, and it has both of those. Southwest flights go out there, too. I’ve been wanting to go there for so long, but never got the chance. I’ve gone to a lot of different islands, but Costa Rica is up there with the places I’ve heard I really need to check out. I can’t wait to get lost out in the forest.”