Chicago is a music city first—and everything else second

Chicago has always been a music city first—and everything else second.

Long before the skyline, the restaurants, or the hotel boom, there were basement jazz clubs, amplified blues bars, warehouse parties, and house tracks pulsing out of the South Side. This city doesn’t just host music—it invents it, lives inside it, and lets it shape the way nights unfold.

In this edition of Off the Record, we’re tuning into Chicago with our friends at Cassette, the go-to music curation agency behind some of the world’s most vibey hotels. You know that moment when you walk into a lobby and instantly Shazam the soundtrack? We bet it was Cassette behind the scenes.

To help map it all out, we sat down with Chicago native and Grammy-winning producer, DJ Paul “DJWS” Blair, whose work spans pop, hip-hop, and electronic music—but whose roots remain firmly planted here. Through his lens, we map a three-day journey across the city, pairing legendary venues with the tracks that still define them.

Drop the needle. This is Chicago, unfiltered.

Producer, DJ, songwriter. Chicago native. Paul “DJWS” Blair has worked across pop, hip-hop, and electronic music, but Chicago is always the throughline. We asked him to map the city the only way that matters: through sound.

You’ve got 72 hours in Chicago—where are you going, and what’s on your playlist along the way?

DAY 1: Green Mill

SONG TO PAIR: “Minnie the Moocher”

This isn’t symbolic, it’s literal history. Cab Calloway was the Green Mill’s most famous headliner during the Prohibition era, and his presence still echoes through the room. Al Capone famously owned a booth with a hidden back exit, a detail that remains part of the club’s lore today.

“Minnie the Moocher” was the ultimate crowd-participation anthem of its time, built around call-and-response sections that demanded audience involvement. That same energy still defines the Green Mill: a room that listens, responds, and moves together.

DAY 2: Teatro ZinZanni

SONG TO PAIR: “Non, je ne regrette rien”

“Non, je ne regrette rien” (“No, I Regret Nothing”) is a 1960 chanson made famous by Édith Piaf, celebrated for its dramatic melody and defiant lyrics about letting go of the past. Its emotional confidence and unapologetic spirit make it a natural pairing for Teatro ZinZanni—a space that blends spectacle, intimacy, and theatrical flair.

Like Piaf’s performances, the experience is timeless and bold, inviting the audience to fully commit to the moment without hesitation or regret.

DAY 3: Kingston Mines

SONG TO PAIR: “Hoochie Coochie Man”

“Hoochie Coochie Man” (1954) essentially codified the Chicago electric blues sound, introducing amplified grit, stop-time swagger, and a band dynamic built on precision and space. The lyrics are delivered like prophecy rather than confession—projecting confidence and authority instead of vulnerability.

Kingston Mines remains one of the last major clubs where this sound is still lived nightly rather than preserved as history. It’s a place where Chicago blues continues to breathe, evolve, and assert itself in real time.

For Rooted in Rhythm: CHICAGO EDITION, Paul “DJWS” Blair draws from the Windy City’s deep musical lineage, blending jazz, blues, house, hip-hop, and soul to capture the rhythm of a place that’s always been several genres ahead.

As a Grammy-winning producer, DJ, and songwriter who’s worked across pop, hip-hop, and electronic music, what is it about Chicago’s music scene that you like?

“Chicago is full of real people. People here do things because they love them. They aren’t afraid to experiment or try new ideas.

House music may be Chicago’s most famous export—it’s the birthplace of the genre—but the city is also home to jazz, blues, hip-hop, and everything in between. In fact, most of the people I work with in Los Angeles originally come from Chicago.”

Some of the best music moments happen in hotels—lobbies, listening rooms, rooftop bars. In Chicago, where have you seen music and hospitality intersect?

“I used to throw a party at the James Hotel—later the 21c Museum Hotel Chicago—in the early 2000s. A lot of iconic Chicago names came through and played records—Virgil Abloh DJ’d, The Cool Kids were there, along with Million Dollar Mano and Hollywood Holt.

The space was small and intimate—maybe 100 people max. I wish there were more of that today.

More recently, the rooftop at The Wit is exciting in the summer, and Soho House Chicago consistently has strong music programming.”

Where are you going to experience the best music Chicago has to offer?

“Because of Chicago’s central location and incredible theater scene, there’s almost always a great show happening somewhere. I’ve got some great shows coming up at The Salt Shed and Metro, and I’m planning to see more in March.”

Where is Chicago’s music scene heading?

“Chicago’s electronic music scene will always start with house. But what makes the city special is its diversity. You can see almost any genre of music—on any night—somewhere in the city.”

What about Chicago’s music scene/culture/energy excites you?

“It’s the diversity and the realness. People here aren’t trying to be flashy or over the top. When artists aren’t making music just for a paycheck—or for the wrong reasons—it comes through. The experience feels more honest.

There’s great music everywhere, but in cities like New York or Los Angeles, people are often trying to “make it.” Chicago artists are also ambitious—but it’s a different mindset. It feels more grounded.”

What’s one intimate or unexpected space in town where you’ve recently experienced incredible music?

“I saw Kraftwerk at the Auditorium Theatre last year, and it was incredible. They’ve been around forever, but they’re one of my favorite bands of all time—and they still put on a show that only Kraftwerk can.”

What are some Chicago musical experiences—big or small—that you think every visitor should have at least once?

“It really depends on the time of year. In the summer, there are shows downtown, in the parks, and across the city. There are incredible venues from Evanston down to the South Side, and all the way west of I-94.”

My go-to will always be the Green Mill. The place is steeped in history. Uptown was essentially the Hollywood of the early 1900s, and parts of it remain almost unchanged a century later. The Green Mill hosts incredible jazz musicians from Chicago and around the world—playing late into the night, nearly every day.

Anchoring the heart of Wicker Park, The Robey has long been part of Chicago’s creative after-hours circuit. Set inside a 1929 Art Deco tower at the intersection of Damen, Milwaukee, and North, the hotel sits steps from record shops, music venues, and late-night haunts that have shaped the neighborhood’s sound.

Even on quieter nights, the energy lingers—locals drifting through the lobby, playlists setting the tempo, and elevators carrying guests up to rooftop nightcaps at The Up Room, where the city hums below. It’s less about the stay itself and more about what surrounds it: a front-row seat to one of Chicago’s most musically fluent neighborhoods.

Read the full hotel review here.

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