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Concerts in Chicago: Your month-by-month live music calendar

Keep up with the best concerts in Chicago in 2020 at the best shows and festivals hitting town each month

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Destroyer Metro
Photograph: Neal O'Bryan

Chicago may not have a fancy nickname to express just how great of a music city it is, but the bounty of concerts and music festivals that take place here speaks for itself. When the weather is warm, there's at least one festival every weekend in Chicago. And no matter what time of year it is, a true music fan will appreciate the dive bars, dance clubs, blues clubs, amphitheaters, arenas and jazz clubs that host amazing performers every day. There's so much going on here that it can be hard to keep track of—that's where we come in. Before you go out to a show, take a look at our month-by-month picks of the best upcoming concerts in Chicago.

This month's best Chicago concerts

Photograph: Ryan Bourque
Music, Folk, country and blues

Buddy Guy

Buddy Guy's Legends, Loop

Most people call January "the first month of the year" or "three weeks of taking my resolutions seriously," but hardcore Chicago blues fans know that it's actually "Buddy Guy month." Throughout the entire month, the legendary bluesman picks up his polka-dot guitar and takes the stage during a residency at the South Loop blues clubs that bears his name. Guy performs every Thursday, Friday, Saturday and Sunday night, with a different supporting act joining him each evening. This year, you'll see Guy paired with 20-year-old Mississippi guitarist Kingfish, local singer Demetria Taylor and veteran singer-songwriter Jimmy Burns. Tickets to Guy's January residency aren't exactly cheap, but witnessing a bonafide blues icon perform in his hometown is the kind of experience that's worth splurging for.

Diane Coffee
Photograph: Alexa Viscius
Music, Rock and indie

Diane Coffee

Hideout, River West/West Town

A former child voice actor who played characters in animated series like Kim Possible and Lilo & Stitch: The Series, Shaun Fleming has tried on plenty of new identities through the albums he's released under the name Diane Coffee. After portraying King Herod in the Lyric Opera's production of Jesus Christ Superstar in 2018, Fleming entered the studio to write an album that deals with the anxieties of life in a digital age. On Internet Arms, Fleming approaches contemporary electro-pop music with the theatricality of his glam rock alter-ego, creating soaring synth-dappled anthems that recall the radio-friendly fare of Robyn and Lykke Li. Here, he headlines a two-night stand at the Hideout, where you might hear the debut of some new tunes.

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CHAI
Photograph: Julien Kelly-Gross
Music, Rock and indie

CHAI + Bunny

Empty Bottle, Ukrainian Village

The four women who make up CHAI hail from Japan, often wear matching pink jumpsuits and have been known to hang out with gigantic Japanese pop stars like Kyary Pamyu Pamyu. But this quartet isn't belting out processed four-part harmonies atop layers of synthesizers—CHAI is a rock band on a mission. On its latest album, PUNK, the group speaks out against the homogenized, hyper-cute "kawaii" beauty culture of Japan, championing individuality and inclusivity atop disco beats and fuzzed-out basslines. Even if you don't understand enough Japanese to decipher every lyric, the spirit of empowerment in CHAI's rebellious anthems is palpable. Local rockers Bunny open the show.

Wu-Tang Clan performs at The Congress Theater, 1/8/11
Photograph: Max Herman
Music, Rap, hip-hop and R&B

GZA

Concord Music Hall, Logan Square

Wu-Tang Clan member GZA—also known as "the Genius"—was the first member of the group to sign an individual record deal (his debut was aptly titled Words from the Genius), but he saved his most memorable tracks for his 1995 release, Liquid Swords. The album was part of the first wave of Wu-Tang solo records, layering GZA's agile lyricism atop the kung-fu movie excerpts and dusty soul samples of producer the RZA. Though he's toured behind the album extensively in recent years, his latest stop in Chicago will bring the 25-year-old songs to life with the help of a live band.

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The Art Institute of Chicago.
Photograph: Courtesy Art Institute of Chicago
Music, Rock and indie

John Cale

Art Institute of Chicago | Chicago, IL, Grant Park

A founding member of the Velvet Underground who went on to dabble in straight-ahead rock, avant-garde composition and classical music, John Cale has a reputation as a daring musician and an adventurous producer. After working on music with contemporary artists like Field Music and Marissa Nadler, Cale recently revisited and reinterpreted his 1982 art rock opus, Music For a New Society. Cale's performance at the Art Institute coincides with the closing of the “From A to B and Back Again” exhibition, which explores the work of artist—and, briefly, the Velvet Underground's manager and producer—Andy Warhol.

Death Cab For Cutie
Photograph: Michael J. Chen
Music, Rock and indie

Benjamin Gibbard + Tara Jane O'Neil

Thalia Hall | Chicago, IL, Lower West Side

After more than two decades, Washington outfit Death Cab For Cutie is still synonymous with the kind of dramatic, lovelorn indie-rock balladry that always seems to find its way into TV soundtracks. Expect to hear plenty of classic Death Cab tunes when Benjamin Gibbard brings his solo tour to Thalia Hall for three nights, performing songs from throughout his memorable catalog. And just because we're completists, we're also hoping to hear a few cuts from Gibbard's full-album cover of Teenage Fanclub’s 1991 power pop classic, Bandwagonesque. Experimental singer-songwriter Tara Jane O'Neils opens the show each night.

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Iron and Wine
Photograph: Piper Ferguson
Music, Folk, country and blues

Iron & Wine + Calexico

Thalia Hall | Chicago, IL, Lower West Side

When Florida folk singer Sam Beam and Latin rock band Calexico teamed up on the In The Reins EP in 2005, the two acts struck gold by marrying Beam's gentle lyrics with grandiose pedal-steel-dappled arrangements. It's no surprise that Beam and Calexico got back together nearly a decade-and-a-half later to records a follow, Years to Burn, which showcases the evolution of both groups of artists. The collection of dusty folk ballads and slow burning rock numbers is another successful collaboration, playing to the strengths of both parties even if it doesn't exactly blaze any new territory. Local singer-songwriter Gia Margaret opens on January 29 and Los Angeles guitar virtuoso Madison Cunningham supports on January 30.

Smart Bar
Photograph: Courtesy Smart Bar
Music, Dance and electronic

Derrick Carter

Smart Bar, Wrigleyville

House music luminary Derrick Carter has been producing and spinning tracks in Chicago since the late ’80s, working behind the counter at DJ destination Gramaphone Records and becoming a Smart Bar resident along the way. Taking a break from his busy touring schedule in Europe (where house music is still a bona fide cultural phenomenon), Carter gets behind the decks for the entire evening on the final evening of January.

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Makaya McCraven
Photograph: David Marques
Music, Jazz

Makaya McCraven

Symphony Center, Loop

Drummer and composer Makaya McCraven is the J Dilla of Chicago's jazz scene, but instead of chopping up his record collection and molding the samples into new beats, he uses tapes of improvised performances to craft taut grooves in the studio. On the heels of his 2018 album, Universal Beings, which found McCraven collaborating with a global cast of players, the bandleader makes his Symphony Center debut with the premiere of a new composition. Entitled "In These Times," the multimedia creation draws inspiration from black activists and musicians, performed with the support of an ensemble that includes Marquis Hill on trumpet, Junius Paul on bass and Greg Ward on saxophone.

The best concerts each month

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