Chicago’s 20 Most Hard-Working Musicians in 2024

2024 has been nothing short of a long year. With all of the ups and downs, one thing is consistent: Chicago has some f****** amazing musicians. As the creator of Chicago Show Calendar, I see first hand how many artists are playing on a daily basis. Because of this, I decided to create a short list of 20 artists who have been making the impossible, possible.

Huge shoutout to all these musicians and every other artist out there with the guts to get on stage and do what they love. And an additional thanks to you, the readers, promotion teams, show-goers, fans, managers, roadies, and EVERYONE else. Live music is important and it would be nothing without you.

Let’s get to it.

1) Lé Bump DJs.

Subterranean and Empty Bottle Boiler Room style sets, a main stage performance at Wicker Park fest, themed parties at Sportman’s Club and Easy Does It, a collaboration pizza with Pizza Friendly Pizza, multiple merch drops including a soccer kit and an airbrushed tote, and a weekly curated newsletter with interviews and item recommendations. What do these things have in common? The Lé Bump DJ team. This group has taken over 2024 and they only have more to show in 2025.

Follow Lé Bump.

2) Woes

Imagine: your walking home from Lollapalooza after a very long day of music with major headliners and you hear from the distance someone rapping. As you continue walking you see a large U-Haul van with the back open and a guy with mic and an amp. How is it that a guy on the side of the road in a U-Haul van had more of a memorable live set than the headliners of Lollapalooza? It takes creativity and guts to try something out and that mixed with a new EP and album in 2025 gets Woes at #2.

Follow Woes.

3) Girl K

Girl K has been making music in Chicago for awhile, but this year felt different for the “Alone With U” pop star. With a brand new album and an accompanying release party at Sleeping Village it’s been a fun year, and with the recent Tik Tok virality of her dad’s break dancing career, the sky is the limit.

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5) DMB

You might know DMB as a transmasc musician giving alt folk sound a revitalization or you might know DMB as a longtime Chicago Reader City Life journalist. Either way DMB is always on the scene and working to extend their craft in writing both for the Reader and for his original music.

Follow DMB.

6) Footballhead

The five piece Footballhead emerged on the scene last year and have quickly been placed on some major bills with bands like Say Anything, Kenny Hoopla, and Superbloom. In between touring as openers and having their own midwestern Headlining tour, they’ve played sets at Logan Square Arts Fest, had an album release party at Sleeping Village, and released new merch.

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4) Amira Jazeera

One of These Days’ 2024 Artist To Watch, Amira Jazeera has been EVERYWHERE this year. From playing festival sets like Taste of Chicago and Pride to a Victorian style music video for her single “Still Thinkin Bout Me”, she’s had a lot going on in 2024 and it seems like 2025 is only going to keep going.

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7) Prosperity Room

To get a residency at The Whistler is no easy feat, but Prosperity Room’s first set in January hit with a bang and ever since the Chicago DJ has been boosting up in popularity. With mixes like Ethel Cain x The 1975, Vanessa Carlton x City Girls, and Paramore x Charli XCX, his unique sound has carried over into a large Tik Tok audience that is only going to increase his popularity as we move into 2025.

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8) Millie Ahearn

Chicago has no shortage of amazing jazz musicians and with tons of jazz clubs in Chicago it can be hard to break through and make a name for yourself. Millie Ahearn has been able to do just that. With a monthly residency at Clara’s and lineup slots at Dorian’s, Epiphany Center for the Arts, Andy’s Jazz Club, The Whistler, and almost every other jazz spot in the city, Millie effortlessly makes her way through solo and collaboration sets and is an exciting addition to Chicago’s rich history of jazz.

Follow Millie Ahearn.

9) Greg Obis

Greg Obis is your favorite Chicago artist’s favorite Chicago artist. From mastering one of the best albums of 2024 in MJ Lenderman’s Manning Fireworks, touring Europe this year with his band Stuck, and running the Chicago based record label Born Yesterday (just to name a few things), people like Greg are the reason Chicago’s music scene continues to be at the forefront of what’s new and next.

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10) The Hoyle Brothers

If you’ve been out on a Friday night in Chicago chances are you’ve stopped into Empty Bottle for the historic Honky Tonk nights. Or maybe if you frequent Sunday afternoons in Lincoln Square you might catch the Sunday Hoyle Brothers’ residency at Martrys’. With tutorials on how to 2-step and true-to-the-original covers of country classics, if you’ve gone to a Hoyle Brothers’ honky tonk you know how much an experience it is.

Follow The Hoyle Brothers.

This write-up is dedicated to Steve Albini. Featured as number 20, his work doesn’t need explanation. As one of the most influential producers of rock music to date, Chicago is lucky to have housed such a legend. His legacy continues on at Electrical Audio studios.

Listen to the full playlist below.