Chicago Jazz Festival/Photo: Walter S. Mitchell III, City of Chicago

While New Orleans was the birthplace of jazz, Chicago has always served as a key hub for America’s most original art form. Between 1915-16, Tom Brown’s Band and Original Dixieland Jazz Band came to Chicago from New Orleans, making Chicago the first major northern city to feature jazz. In 1922, King Oliver brought Louis Armstrong to Chicago. Armstrong lived at 421 East 44th Street for a few years and composed songs like “Cornet Chop Suey” and “Struttin’ With Some Barbecue,” transforming the genre through his improvised solos and scat singing.

Throughout the decades, Chicagoans continued to demonstrate their devotion to this art form. In 1974, Chicago jazz aficionados organized a tribute concert to Duke Ellington in Grant Park, the first of many ad hoc concerts there. The official Chicago Jazz Festival was formed in 1979. Over 125,000 people showed up for the event, and the city decided to make it a permanent fixture.

The 2025 Festival will take place in Millennium Park from August 28-31. The main stage will be the Jay Pritzker Pavilion, and there will also be performances at the nearby Von Freeman Pavilion, the WDCB Jazz Lounge, the Harris Theater Rooftop Terrace and pre-festival events at the Chicago Cultural Center’s Preston Bradley Hall and Claudia Cassidy Theater. While choosing which act to spotlight is like deciding what to order from an all-night diner, here are a few suggestions.

Esperanza Spalding/Photo: Holly Andres

Thursday, August 28

Esperanza Spalding, Jay Pritzker Pavilion, 7:45pm-9pm

After a series of afternoon events at the nearby Cultural Center, the festival’s first night will be headlined by Esperanza Spalding. A five-time Grammy winner, Spalding was selected by Nobel Laureate Barack Obama to be the single artist performing in his honor at the Nobel Peace Prize Concert in 2009. Legend has it that her musical career began at five, when she heard a Beethoven sonata then walked to the piano and reproduced it. Although she’s mastered violin, piano and clarinet, Spalding first gained fame playing the upright double bass, an uncommon choice. Today she’s best known for her vocals, which have been described by New York Times jazz writer Ben Ratliff as “light and high, up in Blossom Dearie’s pitch range, and she can sing quietly, almost in a daydream.” Performing everything from scat to standards to jazzy R&B, her appearance at the Chicago Jazz Festival is a rare opportunity to see this generational talent in an open festival setting.

Monty Alexander/Photo: Jean-Baptiste Millot

Friday, August 29

As mentioned earlier, New Orleans was the birthplace of jazz, and no jazz festival would be complete without a strong helping of music from the Crescent City. To this degree, each day of the festival will be opened by a first and second line performance by the Windy City Ramblers. This has become a recent tradition at the festival, as this Chicago-based, New Orleans-inspired band will dance, march and high step their way across Millennium Park with more than enough energy to jumpstart the day.

The Regulators, Von Freeman Pavilion, 12:40pm-1:35pm

Whether performing as bandleader or arranging for singers like Paul Marinaro, playing and touring with Von Freeman or writing his doctoral thesis on the relationship between race and jazz on Chicago’s South Side, Mike Allemana has been a longtime backbone of the Chicago jazz scene. One of his many endeavors includes his work as co-leader of The Regulators, deviating from the bebop and standards of his other projects by combining free funk and jazz with bedouin, klezmer and Romany modes. Joined by Gerald Dowd and Matt Ferguson on bass, this is a band that will treat your ears like a splash of sriracha.

Marques Carroll Trumpet Summit, Von Freeman Pavilion, 3pm-4pm

Carroll burst into the jazz scene in 2021 with his album “The Ancestors’ Call,” which paid tribute to both his known ancestors in Chicago and those who came before them in Africa. An author, educator and historian, The Trumpet Summit pays tribute, musically and spiritually, to the great trumpeters who preceded them. Expect to hear the sounds of Nicholas Payton, Wynton Marsalis, Clifford Brown, Lester Bowie, and many more of the great trumpeters who have graced the stages of jazz clubs and advanced the sounds of the genre.

Monty Alexander, Jay Pritzker Pavilion, 7:45pm-9pm

While he was still in his teens, Alexander’s piano and social skills earned the admiration and friendship of Frank Sinatra and Miles Davis. The following fifty years have seen him combine the smooth piano of Oscar Peterson and the swing of Count Basie with bebop and cool jazz lines. Born in Jamaica, Alexander often throws in diverse elements of his native country into his music, including a ska/jazz version of the “James Bond Theme” and “No Woman No Cry,” along with standards like “As Time Goes By.” A true entertainer, Alexander’s pre- and post-song anecdotes are almost as entertaining as his music.

Kermit Ruffins/Photo: James Demaria

Saturday, August 30

Jeremy Kahn Trio with Isabella Isherwood, WDCB Jazz Lounge, 4:30pm-6:15pm

Jeremy Kahn is another of a long list of Chicago musicians who may not be marquee names, but are at the top of the go-to musicians’ list. He has answered the call for Max Roach, Dizzy Gillespie, Joni Mitchell, Aretha Franklin, Dee Alexander and Branford Marsalis, to name a few. Smooth and dramatic without being flashy, his piano style blends perfectly with ensembles, trading lines, fours and effortlessly shifting back to the melody. For this performance he will be teamed up with Isabella Isherwood. Another local gem, Isherwood’s vocals are a lyricist’s best friend. With a range that can jump from a whisper to a high octave sustain, Isherwood not only sings, but feels and expresses each syllable of each word, telling a musical story with every stanza.

Kermit Ruffins & the Barbeque Swingers, Jay Pritzker Pavilion, 7:30pm-9:15pm

A founding member of the New Orleans’-famed Rebirth Jazz Band, Ruffins will take over where the Windy City Ramblers left off. Blowing a mean trumpet, Ruffins is a throwback to the soft swinging, bluesy, scatting, but overall happy, joyous and upbeat music of Armstrong, Louis Prima and nearly a century of jazz at Preservation Hall. Capable of blowing a “high C” with the best of them and even singing in a sandpaper scat reminiscent of King Louie, Ruffins throws in touches of zydeco and Creole R&B that will send people dancing all the way home.

Ari Brown

Sunday, August 31

Natalie Scharf Quintet Featuring Paul Asaro, Jay Pritzker Pavilion, 4pm-4:45pm

Once you get to a certain level, every brass and woodwind player can play the notes on all the scales, fast or slow. What differentiates many is the tone, tremolo and embouchure (or the way each note is played). Natalie Scharf exemplifies this. The notes coming out of her tenor sax don’t just come out of her horn; they linger in the air like the smoke from a French cigarette. The same can be said for her bebop lines. Fast, of course, but there is also a certain ring, a certain clarity to them that rings pure. As a longtime member of the Chicago Cellar Boys, she helped to sustain pre-big band, Roaring Twenties swing in Chicago. For the night’s show, she will be continuing in this vein, joined by Paul Asaro, another stalwart of speakeasy swing.

Ari Brown Quintet, Jay Pritzker Pavilion, 6:25pm-7:25pm

In a festival that features everything from rising stars to Louis Armstrong throwbacks, Ari Brown represents another jazz genre: avant-garde, or “free music.” A member of the AACM since 1971, he has performed or recorded with almost every major figure in the free jazz movement, including McCoy Tyner, Anthony Braxton, Lester Bowie, Kahil El’Zabar and Famoudou Don Moye. A longtime Chicago jazz figure, he has recorded over twelve albums for Chicago-based Delmark Records, and performed with local, more traditional jazz and bebop musicians like Orbert Davis and the highly underrated Malachi Thompson. Combining African and Afro-Cuban rhythms with dissonant and modal keyboard and bass lines on songs like “Wayne’s Trane,” his saxophone will soar like the sounds of the Nubian call, floating down the Nile over the centuries.

Chicago Jazz Festival is Thursday, August 28-Sunday, August 31, at multiple locations around Millennium Park, 201 East Randolph, and the Cultural Center, 78 East Washington. Free admission. For more information, go to the Jazz festival event site here.