This year’s Windy City Smokeout music lineup sees up-and-comers, seasoned stars and downright entertainers. Here’s a primer on how – and who – to listen to bringing the hype to this year’s Windy City Smokeout. Be sure to check out below for your full, free playlist, courtesy of Spotify.

shot of the crowd & stage at the smokeout

“In Case You Didn’t Know” – Brett Young

Young’s bona fide hit might be his most tender track, and that’s perfect. It’s love gone right. What’s not to like?

“The Long Way” – Brett Eldredge

Pointed, paced and authentic — Eldredge paints a picture of a helplessly awestruck man and the love interest that leaves him wanting more. “Take me the long way around your town,” he pleads. We’re left wanting more time with this song, too.

“It Ain’t My Fault” – Brothers Osborne

This 2016 chart-topper provides the perfect punch of folksiness, fun and pure renegade-ery. One listen and you’ll be dancing in anticipation of Brothers Osborne’s fest-closing Sunday night set.

“Drinkin’ Problem” – Midland

Midland often follows a familiar beer-drinking formula in their traditional approach, and “Drinkin’ Problem” excels as a classic good-times anthem.

“That Ain’t Country” – Aaron Lewis

This tattooed, formerly alt-metal vocalist works with heavy nostalgia as he paints a portrait of his ideal country day. We’re here for it.

“7 & 7” – Turnpike Troubadours

An Oklahoman collective, TT has a distinctly grassroots sound. It’s on full display with “7 & 7,” a genuine jam about better times past with the hope that one day those times will return. TT’s Sunday night set will make sure of that.

“The Best Is Yet to Come” – Drake White and the Big Fire

Pieces’s standout track has a palpable energy to it, fully displaying White’s dynamic influence. We hear elements of country, blues, rock & roll and reggae, resulting in a fresh sound that seems more than stage-ready.

“A Little Dive Bar in Dahlonega” – Ashley McBryde

With her catchy lyricism and booming voice, McBryde is, quite simply, poised for big things. On this track, she shows her skillful ability to make the local into something universal; we’ve all had our Dahlonega, Georgia.

“What Ifs” – Kane Brown

This hit topped almost every country music chart at one point in 2017, no surprise with its melodic hook complemented by Brown’s robust vocals.

“With You I Am” – Cody Johnson

Johnson is bringing his heavily Southern twang to Chicago on Friday afternoon, seemingly ready to set a romantic mood with tracks like this one, an unapologetic declaration of commitment to the one who catches his eye.

“Runnin’ With An Angel” – Riley Green

Initially feeling upbeat, it quickly becomes clear that this is a song about breakup. That only makes it more profound, a resonant and brutally honest rock ballad.

“Shut Up Kenny” – Walker Hayes

Here the singer pens a direct note to Kenny – yes, Chesney – lamenting the often harsh relatability of the country icon’s music. Hayes’s poppy style makes for a quirky confession that also comes off as uniquely vulnerable. Maybe Chesney will listen one day, but for now, we’re all intently listening to Hayes.

girl on shoulders in the crowd of the smokeout

While these 12 acts are sure to kill it, there are plenty of other artists ready to hold down the stage. Check out the rest of the gems at the festival by listening to Windy City Smokeout’s curated playlist:

Purchase Festival Tickets Here