• Woman in red top and black shorts laughing playing a fun game of pickleball
  • Chicago, IL: Pickleball Ladder Leagues at SPF | Spring 2026
  • Chicago, IL: Pickleball Ladder Leagues at SPF | Spring 2026
  • Chicago, IL: Pickleball Ladder Leagues at SPF | Spring 2026
  • Four young, fun people posing for a selfie with a pickleball court in the background. Four, young cute men posing together on a pickleball court with equipment. Young man playing pickleball on an outdoor court with palm trees in the background, Man playing pickleball on an outdoor court with a fence and trees in the background. Playing in Young woman holding a pickleball paddle on a court with a blurred background. From Silly Pickles pickleball ladder league (the world&
  • Chicago, IL: Pickleball Ladder Leagues at SPF | Spring 2026
  • Silly Pickles pickleball characters (iconic pickle graphics) from the world&
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Chicago, IL: Pickleball Ladder Leagues at SPF | Spring 2026

Hey Chicago! Our OG Sunday night and LGBTQ+ (+ allies!) Monday night pickleball leagues are powered by our partner's website, so click below to use their platform to sign up directly:

Sunday Nights Now Open! Click Here to Sign Up 

Monday Nights Now Open! Click Here to Sign Up

Silly Pickles doesn't take registrations directly through our website for these leagues, so we keep the waitlist live here on purpose - enter your email to be the first to know about new leagues & events in Chicago! 
    Woman in red top and black shorts laughing playing a fun game of pickleball
    Chicago, IL: Pickleball Ladder Leagues at SPF | Spring 2026
    Chicago, IL: Pickleball Ladder Leagues at SPF | Spring 2026
    Chicago, IL: Pickleball Ladder Leagues at SPF | Spring 2026
    Four young, fun people posing for a selfie with a pickleball court in the background. Four, young cute men posing together on a pickleball court with equipment. Young man playing pickleball on an outdoor court with palm trees in the background, Man playing pickleball on an outdoor court with a fence and trees in the background. Playing in Young woman holding a pickleball paddle on a court with a blurred background. From Silly Pickles pickleball ladder league (the world&
    Chicago, IL: Pickleball Ladder Leagues at SPF | Spring 2026
    Silly Pickles pickleball characters (iconic pickle graphics) from the world&

    NEW PADDLES JUST DROPPED

    View all

    NOW LET'S GET SILLY...

    @sillypickles

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    • Man smiling, looking happy holding a pickleball paddle on a court with buildings in the background