Silly Pickles

Browse all Silly Pickles sports sessions in Chicago, IL. Drop-ins, leagues, and more — find your next game on RecNet.

About Silly Pickles

Silly Pickles runs the world’s funnest adult ladder leagues: pickleball and indoor sand volleyball across Chicagoland and beyond, built for meeting people and having fun.

Location: Chicago, IL

Sports and programs: pickleball · Community Group

Official website

Current sessions

• Pickleball Ladder League at SPF Lincoln Park (Sundays)

  2026-12-06T22:00:00.000Z · Sun · 4:00 PM – 11:00 PM · Chicago · SPF

• LGBTQ+ Pickleball Ladder League at SPF Lincoln Park (Mon)

  2026-12-01T00:00:00.000Z · Mon · 6:00 PM – 11:00 PM · Chicago · SPF

• Pickleball Ladder League at SPF Irving Park (Thursdays)

  2026-11-20T00:30:00.000Z · Thu · 6:30 PM – 10:30 PM · Chicago · SPF Pickleball Courts

• Pickleball Ladder League at SPF Irving Park (Sundays)

  2026-12-06T22:00:00.000Z · Sun · 4:00 PM – 7:00 PM · Chicago · SPF Pickleball Courts

• Pickleball Ladder League at Pickleball Kingdom N. Aurora

  2026-11-20T00:00:00.000Z · Thu · 6:00 PM – 10:00 PM · North Aurora · Pickle Ball Kingdom North Aurora

• Pickleball Ladder League at The Picklr Naperville

  2027-01-10 · 1:00 PM – 5:00 PM · Naperville · The Picklr Naperville

• Pickleball Ladder League at FLICKS Pickleball Club

  2026-12-06T21:00:00.000Z · Sun · 3:00 PM – 5:00 PM · Mundelein · FLICKS Pickleball Club

• Pickleball Ladder League at Lucky Shots (Winter 2027)

  2027-01-11T01:00:00.000Z · Sun · 7:00 PM – 10:00 PM · Minneapolis · Lucky Shots Pickleball Club

• Indoor Sand Volleyball Ladder League at Players Sports Center (Winter 2027)

  2027-01-10T21:00:00.000Z · Sun · 3:00 PM – 8:00 PM · Chicago · Players Sports Center