What To Do in Chicago This Week - W/E Oct 5, 2025

What to Do in Chicago — September 29 to October 5, 2025

What to Do in Chicago — September 29 to October 5, 2025

Chicago is packed with concerts, theater, cultural festivals, and seasonal events this week. Here’s your day-by-day guide to the best things to do across the city, with dates, times, locations, and costs included where available.

Disclosure: This post contains affiliate links. As an Amazon Associate, I earn from qualifying purchases. Prices and availability are accurate as of the time of publication and may change.

Monday, Sept 29

1. Candlelight Concert: Coldplay Tribute

When: 7:00 PM
Where: Salvage One, 1840 W Hubbard St
Cost: ~$40
Coldplay’s greatest hits performed by string musicians in a candlelit setting — magical and atmospheric.

Tuesday, Sept 30

2. “Ava — The Secret Conversations”

When: 7:30 PM
Where: Studebaker Theater, 410 S Michigan Ave
Cost: ~$40+
A dramatic play exploring the life and inner thoughts of Hollywood legend Ava Gardner.

Wednesday, Oct 1

3. Colter Wall at Auditorium Theatre

When: 8:00 PM
Where: Auditorium Theatre, 50 E Ida B. Wells Dr
Cost: ~$55+
Canadian country star with a deep voice and gritty storytelling style.

4. Durand Jones & The Indications at The Salt Shed

When: 7:30 PM
Where: The Salt Shed, 1357 N Elston Ave
Cost: ~$40+
Retro-soul band with modern energy — perfect for an intimate night out.

Thursday, Oct 2

5. Queens of the Stone Age — The Chicago Theatre

When: 7:30 PM
Where: The Chicago Theatre, 175 N State St
Cost: ~$75+
Legendary rock band with a thunderous live show in one of Chicago’s most historic venues.

6. Girl Dinner & Tunes with HeyGIRL!

When: 6:00–9:00 PM
Where: Offshore Rooftop, Navy Pier
Cost: Ticketed dinner + entertainment
A trendy night featuring cocktails, tarot, and live DJs overlooking Lake Michigan.

Friday, Oct 3

7. Lincoln Square Ravenswood Apple Fest (Opening Day)

When: 3:00–7:00 PM
Where: Lincoln Ave between Lawrence & Sunnyside
Cost: Suggested $5 donation
Kick off October with apple cider, pies, family fun, and live music at this beloved street festival.

Saturday, Oct 4

8. Dabin in Concert

When: 8:00 PM
Where: Aon Grand Ballroom, Navy Pier
Cost: ~$50+
Electronic artist Dabin delivers an immersive show filled with lights, visuals, and energy.

Sunday, Oct 5

9. Rome Sweet Rome — Chicago Shakespeare Theater

When: 2:30 PM matinee
Where: Chicago Shakespeare Theater, Navy Pier
Cost: ~$86+
A Shakespeare-meets-hip-hop retelling of Julius Caesar with Chicago flair.

10. The Lion King at Cadillac Palace Theatre

When: 2:00 PM matinee
Where: Cadillac Palace Theatre, 151 W Randolph St
Cost: ~$55+
Disney’s Broadway spectacle with incredible music and costumes — a perfect family outing.

Packing & Gear Suggestions for the Week

Disclosure: This post contains affiliate links. As an Amazon Associate, I earn from qualifying purchases. Prices and availability are accurate as of the time of publication and may change.

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