Deadmau5 and Charlotte de Witte both hold down Navy Pier’s East End Plaza, one weekend apart, which makes it the rare city where the same outdoor stage can host two very different electronic nights. Two blocks of the same week offer the opposite: Giancarlo Guerrero leads the Chicago Symphony Orchestra through Fandangos and Enigma Variations at Orchestra Hall on Friday afternoon, a classical bill that sits oddly close to the Broadway tour of Jekyll & Hyde at the Broadway Playhouse.
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- Chicago Symphony Orchestra: Giancarlo Guerrero
- Charlotte de Witte at East End Plaza
- Jekyll & Hyde at Broadway Playhouse
- Waitress at the Nederlander
- A Wrinkle in Time at Lifeline Theatre
- Summer Walker at Credit Union 1 Arena
- King’s X at House of Blues
- Play On! at Chicago Shakespeare
- Red Line Jazz Festival at Harris Theater
Chicago Symphony Orchestra: Giancarlo Guerrero
Fri, Oct 16, 1:30 PM · Orchestra Hall At Chicago Symphony Center · from $51
The CSO opens the weekend at Orchestra Hall with Guerrero on the podium, playing Fandangos and Elgar’s Enigma Variations. It is a matinee-length chance to hear one of the country’s great orchestras in its home room.
Charlotte de Witte at East End Plaza
Fri, Oct 16, 4:00 PM · East End Plaza at Navy Pier · from $103
Belgian techno artist Charlotte de Witte is one of the genre’s best-known names, and her Friday set on the open-air plaza at Navy Pier is built for a loud, late crowd. Expect driving four-on-the-floor rhythms under the lakefront sky.
Jekyll & Hyde at Broadway Playhouse
Fri, Oct 16, 7:00 PM · Broadway Playhouse at Water Tower Place · from $146
Frank Wildhorn and Leslie Bricusse’s musical adapts Stevenson’s novella into a rock-inflected score with a big voice-driven cast. It suits anyone who wants a full night of theatre with a strong dual-role showcase.
Waitress at the Nederlander
Fri, Oct 16, 7:00 PM · Nederlander Theatre at Ford Center for the Performing Arts · from $74
Sara Bareilles’s musical about a waitress baking pies to escape her life has a warm, bittersweet score and a devoted following. The Nederlander is a classic Loop house, so the staging is well suited to an easy Friday night out.
A Wrinkle in Time at Lifeline Theatre
Fri, Oct 16, 7:30 PM · Lifeline Theatre · from $66
Madeleine L’Engle’s novel becomes an intimate, family-friendly musical at Lifeline, a small Rogers Park theatre known for adventurous stories. It is a good pick for a smaller, more personal evening.
Summer Walker at Credit Union 1 Arena
Fri, Oct 16, 7:30 PM · Credit Union 1 Arena · from $90
Summer Walker is one of R&B’s most successful recent voices, with intimate songwriting that plays very well to a large crowd. The arena setting on the West Side gives the show room for a full production.
King’s X at House of Blues
Fri, Oct 16, 7:00 PM · House Of Blues – Chicago · from $30
King’s X are a veteran Houston trio whose layered harmonies and heavy grooves have earned them a loyal cult following across decades of hard rock. The House of Blues room is a good fit for a loud, old-school night.
Play On! at Chicago Shakespeare
Fri, Oct 16, 7:00 PM · The Yard at Chicago Shakespeare Theatre · from $140
Play On! is a musical reimagining of Shakespeare’s Twelfth Night set to Duke Ellington’s music, staged in the Yard at Chicago Shakespeare on Navy Pier. It blends a classic text with jazz standards.
Red Line Jazz Festival at Harris Theater
Fri, Oct 16, 7:30 PM · Harris Theater · from $55
The Red Line Jazz Festival brings a line-up of jazz and blues performers to the Harris Theater in Millennium Park. It is a polished, seated setting for listeners who want a grown-up Saturday.
Check dates and times before you go, since a few shows run in different rooms on the same night. Booking early is wise for the Chicago Symphony and Waitress, which tend to sell out.







