Things to Do in Chicago This Weekend: Sep 18–20

Things to Do in Chicago This Weekend: Sep 18–20 City Guides
Riot Fest dominates Douglass Park with Twenty One Pilots and Tool anchoring three days of alternative and metal mayhem, while the city's theaters and smaller venues offer everything from Phoebe Bridgers at the United Center to intimate blues and folk performances.

Riot Fest takes over Douglass Park this weekend with Twenty One Pilots, Tool, and Pierce The Veil commanding the festival’s three-day run—but Chicago’s stages stretch far beyond the festival grounds. The Chicago Symphony Orchestra opens Friday with Schumann and Mendelssohn at Orchestra Hall, while theaters across the city premiere musicals and plays that rival the festival’s scale and ambition.

Tip: code GTIX20 takes 20% off ticket prices on every event below — no minimum and no expiry.

Riot Fest Chicago: Twenty One Pilots, Tool & Pierce The Veil

Fri, Sep 18, 3:30 AM · Douglass Park · from $362

Three days of alternative rock, metal, and post-hardcore at Douglass Park with some of the decade’s most commanding performers. Tool’s prog-metal precision and Twenty One Pilots’ genre-bending intensity anchor a lineup that spans everything from established acts to rising names, making this the weekend’s gravitational center for rock fans.

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Phoebe Bridgers at the United Center

Fri, Sep 18, 7:30 PM · United Center · from $54

The indie-folk virtuoso brings her haunting, orchestral arrangements to Chicago’s largest rock venue Friday night. Expect intimate songwriting scaled to arena dimensions—a rare collision of vulnerability and spectacle that defines her live presence.

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Chicago Symphony Orchestra: Petr Popelka & Hilary Hahn

Fri, Sep 18, 1:30 PM · Orchestra Hall At Chicago Symphony Center · from $30

Violinist Hilary Hahn joins conductor Petr Popelka for Schumann, Mendelssohn, and Dvořák at Orchestra Hall on Friday afternoon. This is classical music at its most direct—three Romantic-era masters performed by musicians who understand every note’s emotional weight.

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Jekyll & Hyde at the Broadway Playhouse

Fri, Sep 18, 7:00 PM · Broadway Playhouse at Water Tower Place · from $79

The musical adaptation of Robert Louis Stevenson’s psychological thriller opens Friday night at Water Tower Place with full orchestral accompaniment. Expect Gothic atmosphere, vocal fireworks, and the kind of theatrical spectacle that justifies a night on Broadway.

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Dirty Dancing at the Nederlander Theatre

Fri, Sep 18, 7:00 PM · Nederlander Theatre at Ford Center for the Performing Arts · from $87

The beloved film becomes a stage musical with all the iconic moments intact—the lift, the soundtrack, the summer-camp romance. This is comfort-food theater that works because the source material is timeless and the choreography honors what made the original unforgettable.

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Gary Clark Jr. at the Vic Theatre

Fri, Sep 18, 7:30 PM · Vic Theatre · from $83

The Texas blues guitarist brings his searing tone and modern sensibility to the Vic on Friday night. Clark Jr. plays with the precision of a jazz musician and the raw power of a blues traditionalist—expect extended solos and the kind of guitar work that justifies standing room.

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Aldous Harding at Thalia Hall

Fri, Sep 18, 8:00 PM · Thalia Hall · from $31

The New Zealand singer-songwriter performs at Thalia Hall on Friday with her distinctive blend of folk, art-pop, and theatrical presence. Her voice moves between whisper and wail; her arrangements surprise at every turn—intimate and strange in equal measure.

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Topdog/Underdog at Steppenwolf Theatre

Fri, Sep 18, 7:30 PM · Downstairs Theatre At Steppenwolf Theatre – Chicago · from $139

Suzan-Lori Parks’ Pulitzer Prize–winning play opens at Steppenwolf’s Downstairs Theatre Friday night, exploring race, masculinity, and survival through two brothers and a con game. This is contemporary American drama at its most urgent and inventive.

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Alok (Alok Vaid-Menon) at the Vic Theatre

Sat, Sep 19, 7:00 PM · Vic Theatre · from $48

The gender-nonconforming comedian and performance artist brings their incisive, hilarious take on identity, desire, and culture to the Vic on Saturday. Alok’s comedy is intellectual without being cold—sharp observations wrapped in warmth and genuine curiosity about how we live.

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Beth Hart at the Riviera Theatre

Sat, Sep 19, 8:00 PM · Riviera Theatre – IL · from $63

The powerhouse blues-rock vocalist performs at the Riviera on Saturday night with the kind of emotional intensity that fills a room without amplification. Hart’s voice is her instrument—raw, precise, and capable of breaking hearts in a single phrase.

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Dates and times vary across venues; book early for Riot Fest and the larger theaters. Most shows sell out or approach capacity by Friday afternoon.