While in the Windy City for a big music festival this week, one of the biggest names in Country music stopped by one of the most popular tourist spots in Chicago, but it didn't go as planned.

This Chicago Tourist Attraction Can Be Terrifying, Even for Rock Stars

If you've ever taken the ride to the top of the Sears Tower (i still refuse to call it the Willis Tower), it can be a terrifying experience for anyone who has claustrophobia or a fear of heights.

READ MORE: Country Star Brings Big Voice to Illinois for Free August Concert

It's a tight fit when there's a full elevator heading up 103 floors, which can seem like it takes forever if you're uncomfortable in tight spaces.

And then when the doors open, you are literally up in the sky, with windows at every corner overlooking the city of Chicago and Lake Michigan.

Country Star Has Fear Factor Moment

During an evening out exploring the city of Chicago before his Thursday night headlining performance at Lollapalooza, country music superstar Luke Combs and members of his crew visited the Willis Tower observation deck.

In a video posted to the Luke Combs HQ page on Instagram, friends and entourage members are daring Combs to step out onto the glass "Ledge."

In the viral moment, Combs said he would pose for a picture showing him "NOT" out on the window ledge that's over 1,300 feet above the Chicago streets. "I'm so excited to not go out on that," Combs added.

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The country mega-star is the Thursday night (7/31) headline act at Lollapalooza 2025 held in Chicago's Grant Park.

Combs Pays Tribute to Beloved Cubs Star During Encore

While watching the live stream of Lolla on Hulu, there was a great moment when Luke Combs returned to the stage for an encore, where he played his hit cover of 'Fast Car' wearing a Chicago Cubs #23 jersey with Sandberg on the back.

Former Cubs star Ryne Sandberg passed earlier this week after a battle with cancer.

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