Events in Oswego, Illinois

7 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.

What's coming up

• Oak + Bean Fall Wine Fest
  Sat 17 Oct 2026, 4:00 PM — Festival
  Oak + Bean · 100 West Washington Street, Oswego, IL 60543
• Sweetest Day Date Night
  Sat 17 Oct 2026, 6:30 PM — Live music
  Massage By Tamiko · 123 W. Washington St Suite B12, Oswego, IL 60543
• Boost Your Project Management Techniques Training in Oswego, IL
  Fri 23 Oct 2026, 9:00 AM — class
  Regus · Oswego, Oswego, IL 60503
• Teen Night
  Fri 23 Oct 2026, 6:00 PM — Meetup
  Oswegoland Senior and Community Center · 3525 Walter Payton Memorial Highway, Oswego, IL 60543
• HUNKS The Show at Nash Vegas Saloon (Oswego, IL) 11/03/26
  Tue 3 Nov 2026, 8:00 PM — Live music
  Nash Vegas Saloon · 61 Main Street, Oswego, IL 60543
• Teen Night
  Fri 20 Nov 2026, 6:00 PM — Meetup
  Oswegoland Senior and Community Center · 3525 Walter Payton Memorial Highway, Oswego, IL 60543
• Boost Your Project Management Techniques Training in Oswego, IL
  Fri 27 Nov 2026, 9:00 AM — class
  Regus · Oswego, Oswego, IL 60503

Listings are seeded from venue and organiser calendars. See them on the map.