Things to Do in Chicago This Weekend: Sep 25–27

Things to Do in Chicago This Weekend: Sep 25–27 City Guides
From post-punk intensity at Metro Chicago to orchestral sophistication at Symphony Center, this weekend spans classical masterworks, theatrical productions, and electronic dancefloors across the city's most eclectic venues.

Cold Waves XIV descends on Metro Chicago on Friday with Stabbing Westward and Pig commanding the post-punk stage, while just blocks away the Chicago Symphony Orchestra opens at Orchestra Hall with Klaus Makela conducting Sibelius and Shostakovich. The collision between those two nights—raw industrial energy and refined orchestral precision—captures what makes this weekend so textured.

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

Cold Waves XIV: Stabbing Westward & Pig

Fri, Sep 25, 7:00 PM · Metro Chicago · from $96

Chicago’s premier post-punk and industrial festival returns with three days of uncompromising music. Stabbing Westward and Pig anchor Friday’s lineup, bringing the kind of sonic intensity and theatrical presence that defined the genre. If you’ve been waiting for a room full of people who speak this language, this is it.

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Chicago Symphony Orchestra: Klaus Makela – Sibelius & Shostakovich

Fri, Sep 25, 1:30 PM · Orchestra Hall At Chicago Symphony Center · from $71

Conductor Klaus Makela leads the CSO through two of the 20th century’s most powerful voices: Sibelius’s brooding Finnish landscapes and Shostakovich’s defiant modernism. This is orchestral music that doesn’t whisper—it commands, questions, and transforms the room around you.

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Jekyll & Hyde at Broadway Playhouse

Fri, Sep 25, 7:00 PM · Broadway Playhouse at Water Tower Place · from $81

The musical adaptation of Robert Louis Stevenson’s psychological thriller brings duality and darkness to the stage with full orchestral accompaniment. Expect Gothic atmosphere, soaring melodies, and the kind of theatrical spectacle that makes a night out feel like an event.

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Beyond The Gate: Cate Le Bon & Horsegirl

Fri, Sep 25, 6:00 PM · Bohemian National Cemetery · from $74

Indie rock’s most inventive voices converge at Bohemian National Cemetery for an outdoor evening. Cate Le Bon’s art-rock sophistication and Horsegirl’s Chicago-rooted experimental pop create a pairing that rewards close listening and rewards the willingness to be surprised.

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Martin Lawrence

Fri, Sep 25, 8:00 PM · Arie Crown Theater · from $85

The legendary comedian brings his unfiltered energy and decades of material to Arie Crown Theater. Lawrence’s live shows are unpredictable, generous, and built on the kind of comedic timing that only comes from years of commanding a room.

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Sun Ra Arkestra

Fri, Sep 25, 7:00 PM · Constellation – Chicago · from $150

The Arkestra carries forward Sun Ra’s visionary legacy—a collision of bebop, free jazz, and cosmic philosophy that feels equally at home in a small room like Constellation as it does in concert halls. Their music is a conversation between past and future, always in motion.

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Nick Hakim

Fri, Sep 25, 8:00 PM · Lincoln Hall · from $61

The Brooklyn-based R&B and soul artist brings intricate production and vulnerable vocals to Lincoln Hall. Hakim’s music sits at the intersection of electronic sophistication and deeply human emotion—the kind of set that rewards both dancing and standing still.

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Topdog/Underdog at Steppenwolf Theatre

Fri, Sep 25, 7:30 PM · Downstairs Theatre At Steppenwolf Theatre – Chicago · from $129

Suzan-Lori Parks’s Pulitzer Prize-winning play explores identity, race, and brotherhood through two characters and a single room. Steppenwolf’s production cuts to the bone of what makes this play essential: its language, its tension, and its refusal to look away.

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Paula Cole

Fri, Sep 25, 8:00 PM · Thalia Hall · from $10

The 90s alternative-rock icon and multi-Grammy winner brings her distinctive voice and catalog to Thalia Hall. Cole’s music—introspective, rhythmically inventive, emotionally direct—feels more vital now than ever, and a room this intimate lets every note land.

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San Holo

Fri, Sep 25, 10:00 PM · Radius – IL · from $45

The Dutch electronic producer and vocalist brings genre-defying production to Radius, blending ambient soundscapes with dance-floor energy. San Holo’s live sets are immersive experiences—the kind of night where the music surrounds you and time dissolves.

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Dates and venues span Friday through Sunday across the city—check each event’s details for exact times and locations. Book early for the larger venues; smaller rooms often fill quickly on weekends.