Comedy in Chicago
Stand-up, improv, late sets from the names on the posters.
Big Irish Jay at Riddles Comedy Club
Big Irish Jay Hollingsworth headlines Riddles Comedy Club for a full weekend of stand-up. $25 cash cover, two-drink minimum.
Monique Marvez at Riddles Comedy Club
Comedy veteran Monique Marvez brings her fearless, no-holds-barred stand-up to Riddles Comedy Club. Three nights of shows. $25 cash cover.
ARC Music Festival
ARC Music Festival brings Chicago's underground electronic scene above ground—this is where the city's most respected selectors (think Green Velvet, Honey Dijon, Carl Craig) command massive sound systems across Union Park. You'll experience three days of techno, house, and experimental beats in a festival setup that feels more intimate than massive, with the kind of lineup that attracts serious dancers and curious newcomers alike.
Big Thief
Big Thief's bringing that hypnotic, guitar-driven indie folk-rock to Salt Shed's sprawling Goose Island space—the kind of performance where you'll find yourself completely absorbed by Adrianne Lenker's haunting vocals and the band's intricate arrangements. This all-ages show lets you catch one of the most compelling songwriters of our generation in a venue that actually does justice to their dynamics, whether you're posted up in the indoor theater or catching the warm evening air in the outdoor fairground.
Cruising The Waves Yacht Party
You're floating down the Chicago River and out onto Lake Michigan while a top-shelf open bar keeps the good times flowing—and then Navy Pier's fireworks explode across the skyline right in front of you. This inaugural yacht experience pairs live DJs, dinner, and unobstructed water views with the kind of vantage point landlubbers will never have.
Barry Laminack at Riddles Comedy Club
Barry Laminack is funny as ever. Two nights, two shows each: 7:30PM and 9:30PM. 21+ with photo ID. Cash venue only.
Lollapalooza 2026
Four days of the biggest names in music take over Grant Park for Lollapalooza 2026. 170+ bands across 8 stages, street food, after-shows at venues acr
The Crazy & Spontaneous Tour at Riddles
Runnin' Outta Time with Jnine Comedy Special. Two nights featuring Shamika Finley, John David, Big Herc, and live performances. $25 cash cover. 21+ wi
& Juliet: The Musical
& Juliet flips Shakespeare's tragedy into a fever dream of pure pop euphoria—imagine Juliet center stage, taking control of her own story while Max Martin's greatest hits soundtrack every defiant moment. You'll spend two hours in the Loop's architectural masterpiece, The Auditorium Theatre, watching a cast that moves like they're powered by pure adrenaline, as decades of pop bangers (we're talking Britney, The Weeknd, Ariana Grande) propel a narrative that's equal parts romance and rebellion.
Drew Thomas at Riddles Comedy Club
Drew Thomas headlines Riddles Comedy Club. Two nights of stand-up at 7:30 PM and 10 PM. $25 cash cover, two-drink minimum.
Pitchfork Music Festival 2026
Three days of indie, hip-hop, and electronic music curated by Pitchfork in Union Park. Smaller than Lolla, weirder than Riot Fest, and exactly the vib
Quincy Carr at Riddles Comedy Club
The Quality Comedy King Quincy Carr brings the laughs to Riddles. Two shows: 7PM and 9:30PM. $25 cash cover. 21+ with photo ID. Cash venue only, ATM o
Taste of Chicago 2026
Chicago's legendary food festival returns to Grant Park with five days of the city's best restaurants, food trucks, and pop-ups. Free admission to the
Horse Meat Disco: Pride
Horse Meat Disco takes over Metro's Wrigleyville stage for Pride weekend, and you're walking into the kind of queer disco institution that's built a cult following across continents—think euphoric breakbeats, relentless energy, and a crowd that actually knows how to dance. Metro's historic bones (the same stage that's hosted decades of live acts) transform into pure disco hedonism for the night, where the dance floor becomes its own thing entirely.
Weird Al Yankovic: Bigger & Weirder Tour at United Center
The undisputed king of comedy songs returns with his Bigger & Weirder 2026 tour.
Kurt Vile & the Violators
Kurt Vile's threading hypnotic guitar work and deadpan vocals through the Salt Shed's expansive indoor-outdoor setup hits different—especially with the Violators locked in behind him. You're getting the kind of indie rock set that rewards close listening even when you're mobile between the fairground's open air and climate-controlled interior, catching the breeze off Goose Island while the reverb-heavy arrangements wash over you.
Special K Live - Karl Douglas
Special K Karl Douglas, actor, comedian, radio legend from the Rickey Smiley Morning Show. Over 1000 live comedy shows performed. Seen on Sherri, Tubi
Julie Doiron, Carson McHone
Julie Doiron's whisper-soft vocals paired with Carson McHone's understated Americana make for an unexpectedly perfect pairing—expect hushed, introspective songwriting that'll make you forget about your phone for two hours. You'll catch them at Empty Bottle in Ukrainian Village, the kind of room where every acoustic guitar line hits different.
You Set Me Up!: Live Comedy Dating Gameshow at The Hideout
You Set Me Up! — a live comedy dating gameshow at The Hideout. Watch real people get set up on dates by their friends, with comedians and crowd chaos.
Drunk Dracula Interactive Theater
Theatrical drinking game comedy. Audience participation, rowdy prompts, hilarious Dracula-themed show.
Guy Torry Live - Fathers Day Weekend
Fathers Day weekend with the best of the best Guy Torry live. Two shows at 7:00 PM and 9:30 PM. Doors open at 6:30 PM. 21 plus with photo ID. Cash ven
Juneteenth Takeoff w/ Odeal & Mannie Fresh
Mannie Fresh is bringing the legendary beat-making energy to Chicago for a proper Juneteenth celebration—expect two nights of bounce, hip-hop, and the kind of live performances that remind you why summer in this city hits different. You'll be surrounded by the city's best crowd, moving from 6 PM to midnight both nights as Odeal and crew keep the momentum going.
Marco Lavell Live
Marco Lavell live stand-up comedy at Riddles Comedy Club. 7:00 PM to 10:00 PM. Doors open at 6:30 PM. 21 plus with photo ID. Cash venue only. Free par
The Gong Show Hosted by BLT
The Gong Show hosted by BLT at Riddles Comedy Club. Doors open at 6:30 PM. 21 plus with photo ID. Cash venue only. Free parking.
Son Little
With special opening act Tonina. All sales are final, no refunds/exchanges permitted, but tickets may be transferred through your TM Account. Garcia's is fully ADA compliant featuring wheelchair lifts and ramps between the various levels of the venue, assisted listening devices upon request, and allows official service animals. Premium Table seating is located closest to the stage offering the most intimate music experience for guests and includes table service. Reserved Table seating is located on our main floor, behind the Premium section, and also includes table service. Both Premium and Reserved table seating is cabaret style which means you may be sitting with other fans. Private Booths are available and depending on the booth seats 1 to 4, 5, or 6 guests. General Admission/Standing Room is located around the sides of the room on an elevated level for quality viewing and easy bar access. 21 & Over Show. Must be 21+ with a valid ID to purchase alcohol. At Garcia's Chicago.
R&B vs TRAP Bingo with Comedian ThankYouChris
R&B vs TRAP Bingo with big prizes and comedian ThankYouChris bringing the laughs. Doors open at 7:00 PM. 21 plus. Cash venue only. Free parking.
Pour Minds Podcast: Still Sippin' Tour
At Park West.
Mike Lebovitz at Zanies
Chicago comic Mike Lebovitz headlines Zanies. Sharp, dark, and fiercely funny — a staple of the Chicago comedy scene.
An Evening with John Cusack & Screening of Grosse Pointe Blank
John Cusack live Q&A and Grosse Pointe Blank screening. Auditorium Theatre. Jun 13.
Santana & The Doobie Brothers - Oneness Tour 2026
Please note: This event is rain or shine. Parking is sold separately from concert tickets. You will need to purchase a parking pass if you plan to park at the venue. At Credit Union 1 Amphitheatre.
Jack Bensinger at The Hideout
Stand-up comedian Jack Bensinger performs late night at The Hideout. Sharp, clever comedy in one of Chicago's most unique rooms.
Harlem Hayfield, Margo MacEro, Little Victory, Joel Gragg
At Reggies Music Joint.
Hot Sauce Poetry and Comedy Night
Spoken word and stand-up comedy with full Southern soul food menu. Soulful, intimate, hilarious. 7:30PM Friday in Bronzeville.
Fire and Ice Live by Broke But Famous
Broke But Famous Presents Fire and Ice Live. Shows at 7:30 PM and 9:30 PM. Doors open at 7:00 PM. 21 plus. Cash venue only. Free parking.
Billy Eichner
Billy Eichner brings his unhinged, rapid-fire comedy to Lincoln Square's beloved Old Town School of Folk Music—yes, *that* Billy Eichner, the guy who ambushes celebrities on the street and somehow makes it hilarious. Expect relentless energy, sharp cultural commentary, and the kind of performance that'll have you laughing so hard you forget you're in a folk music venue.
Jeremy Piven
At Chicago Improv - Schaumburg.
Chicago Blues Festival 2026
The world's largest free blues festival celebrates the genre Chicago helped define. Three days in Millennium Park with legendary headliners, up-and-co
Pleasantries, When We Was Kids, Middle Seat
Pleasantries, When We Was Kids, and Middle Seat take over Reggies Music Joint on June 12.
Kenny Mason - American BULLDAWG Tour
At Reggies Rock Club.
Don Toliver: Octane Tour
Don Toliver brings the Octane Tour to United Center on June 11.
Wait Wait... Don't Tell Me!
You'll catch NPR's sharpest news quiz show live at The Studebaker Theater in The Loop—expect the kind of rapid-fire wit and unexpected tangents that make the broadcast magic, amplified by a room full of people equally obsessed with current events and terrible puns. The energy is pure controlled chaos: panelists riffing, audience laughing, the whole thing crackling with that "anything could happen" feeling you only get at a live taping.
Mumford & Sons - Prizefighter Tour Platinum
Mumford & Sons bring the Prizefighter Tour to Wrigley Field on June 10.
South Loop Stand Up at Reggies
South Loop Stand Up comedy night at Reggies. Local comedians take the stage at this weekly comedy showcase in the South Loop.
Vincen García & Delvon Lamarr Organ Trio
Vincen Garcia and Delvon Lamarr Organ Trio bring the heat to Garcia's Chicago on June 8.
Vip Stadium Tour
Take the VIP Stadium Tour of Soldier Field on June 7.
Kbong & Johnny Cosmic
Kbong and Johnny Cosmic bring laid-back reggae vibes to Garcia's Chicago on June 7.
Nando de La Gente: En Espanol
Nando de La Gente brings his En Espanol show to Chicago Improv in Schaumburg on June 6.
Midnight Comedy Jam at Laugh Factory
Late-night stand-up comedy. Rowdy, loud, festive. Two-drink minimum. Midnight show Saturday.
Eddie Pepitone — Special Event at Zanies
Eddie Pepitone brings his legendary rage-fueled comedy to Zanies. The Bitter Buddha himself — one of comedy's most original voices.
Improv Comedy Showcase at The Second City
Sketch comedy and improv at Chicago's legendary Second City. Hilarious, dynamic, cultured. Evening shows after 7PM, late-night 10PM slots. Full theate
Comedy venues
Al's #1 Italian Beef (Taylor Street)
Annoyance Theatre & Bar
Apollo Theater Chicago
Birrieria Zaragoza
Bronzeville Soul
Chicago Improv
City Winery Chicago
Cole's Bar
Cornservatory Theatre
De Maat Theatre at Second City
Den Theatre
Gallery Cabaret
Golden Wok
Hideout
iO Theater
Laugh Factory Chicago
Lincoln Hall
Lincoln Lodge
Logan Square Improv
Manny's Cafeteria & Delicatessen
Martyrs'
Park West
Riddles Comedy Club
