Things to Do in Chicago This Weekend: Oct 23–25

Things to Do in Chicago This Weekend: Oct 23–25 City Guides
A weekend of Lyric Opera at the Lyric Opera House, Tedeschi Trucks Band at the Chicago Theatre, Lil Yachty at Radius, and a mix of musicals and comedy across the city.

Friday night puts Tedeschi Trucks Band on the Chicago Theatre’s stage while Lyric Opera opens Omar at the Lyric Opera House, a pairing of blues-rooted virtuosity and grand opera that rarely shares a single evening. The rest of the weekend moves from Wicked-style Broadway at Cadillac Palace to Lil Yachty at Radius and Chicago Philharmonic’s Edward Scissorhands at Auditorium Theatre.

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

Tedeschi Trucks Band at The Chicago Theatre

Fri, Oct 23, 7:30 PM · The Chicago Theatre · from $143

The blues-rock and soul outfit led by Derek Trucks and Susan Tedeschi is known for long, loose, deeply musical sets. The Chicago Theatre’s gilded hall suits a band that rewards close listening.

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Lyric Opera of Chicago: Omar

Fri, Oct 23, 7:00 PM · Lyric Opera House – IL · from $84

Lyric Opera opens its season with a new production in one of the city’s most celebrated houses. It is a rare chance to hear a full opera company at work on a Friday night.

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Red Bull Setlist: Lil Yachty at Radius

Sat, Oct 24, 7:00 PM · Radius – IL · from $37

Lil Yachty is one of the most recognizable names in rap and pop, known for genre-blending hits. Radius offers an intimate room for a Red Bull Setlist performance, so expect a closer view than an arena show.

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The Book Of Mormon at Cadillac Palace

Fri, Oct 23, 7:00 PM · Cadillac Palace · from $117

The Tony-winning musical from the creators of South Park is a sharp, irreverent comedy with memorable songs. Cadillac Palace is a classic Broadway house, and the show plays well for first-timers.

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Chicago Philharmonic: Edward Scissorhands In Concert

Sat, Oct 24, 7:30 PM · Auditorium Theatre – IL · from $54

Danny Elfman’s score for Tim Burton’s film is performed live alongside the story, a strong pick for a fall weekend. The Auditorium Theatre’s historic acoustics suit a film-in-concert program.

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Memphis – The Musical at Studebaker Theater

Sat, Oct 24, 7:30 PM · Studebaker Theater · from $125

Memphis follows a 1950s Memphis radio DJ and a rising Black singer, with a soulful, rhythm-and-blues score. The Studebaker is a comfortable, intimate space for a show with big vocal numbers.

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Jekyll & Hyde at Broadway Playhouse

Fri, Oct 23, 7:00 PM · Broadway Playhouse at Water Tower Place · from $112

Frank Wildhorn’s musical adaptation of Stevenson’s novella is a powerhouse for strong voices and dramatic storytelling. The Water Tower Place venue makes it an easy pairing with an evening downtown.

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Gilla Band at Bottom Lounge

Fri, Oct 23, 7:00 PM · Bottom Lounge · from $47

The Irish post-punk band brings a restless, abrasive energy that suits a club crowd. Bottom Lounge is a well-loved room for guitar-driven acts.

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Maggie Rose at Garcias Chicago

Fri, Oct 23, 8:00 PM · Joe’s Bar On Weed St. · from $30

Maggie Rose is a country-soul singer with a warm, roadhouse-style voice. Garcias offers a relaxed setting for an acoustic-leaning night of roots music.

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Randy Feltface at Vic Theatre

Fri, Oct 23, 7:00 PM · Vic Theatre · from $54

Randy Feltface is a character-driven comedian and musician known for quick, offbeat sketches. The Vic Theatre gives the show a lively room for a Friday laugh.

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Check dates and times before you head out, and book early for Lyric Opera and the Chicago Theatre, which tend to sell out.