Things to Do in West Loop, Chicago Saturday Night, Halloween Weekend 2026

Saturday night, Oct 31 · 12 picks hand‑checked by Stumblday against organizer pages · 1 free in the top 10 · updated Nov 2

The 10 best things to do in West Loop, Chicago on Saturday night, Oct 31

  1. Theater of the Mind — Fri, Nov 13 · Tickets from $69 · Downtown
  2. Drunk Shakespeare: Drunk Dracula (21+ Event) — Fri, Nov 6 7:00pm · Downtown
  3. Death By Disco: Chicago's Biggest Halloween Pop-Up — Fri, Oct 30, 8pm–2am; Sat, Oct 31, 8pm–1am · City Hall and Morgan MFG
  4. ART on THE Mart — Thursdays through Sundays, 7:30–8:00 PM · Free · Downtown
  5. The Winter's Tale — Sat, Nov 7 7:00pm · Downtown
  6. Akeem Ali – The Texture Tour — Sat, Oct 31 7:00pm · Downtown
  7. Haunted House Party at Shedd Aquarium — Sat, Oct 31 7:00pm · Downtown
  8. Swmrs, North By North, Repent — Sat, Oct 31 9:00pm · Downtown
  9. Skalloween Ft. Noskalgia, Local Legends, Rude Echos — Sat, Oct 31 8:00pm · Downtown
  10. City Cruises Chicago Seadog Haunted River Tour — Fri, Oct 30 3:00pm · $37 – $60 · Downtown

More on Saturday night

About this list

Stumblday's hand-checked ranking of the best things to do in West Loop, Chicago on Saturday night of Halloween weekend, Oct 31: 12 picks, refreshed weekly.

More this weekend across Chicago