Chicago, Illinois

Chicago, Illinois

READY TO GET SILLY?

We run the world's funnest leagues.

Join solo or with friends for organized weekly games, friendly competition, and a community you'll actually want to hang out with.

Playing is easy. Making friends is even easier 🤪

LEAGUE DETAILS

  • Regular Season Play

    Most seasons run 6–8 weeks. Find dates, and times listed on each league page, depending on your season!

  • Our Ladder Format

    Each week, you’ll play within a new group of 4 people for one hour at your skill level.

    If you come solo, expect to leave with friends - you'll play each game with a new partner!

  • Easy Scheduling

    If you need to miss a week, no problem! 📅 Just use our weekly RSVP to let us know.

    Need a sub? Just click through our system to request one.

  • Weekly Re-Ranking

    Submit your points after each set of games.

    We’ll use your scores to update your ranking, so matchups are fun and accurate every week!

  • All Skill Levels Welcome

    Our ladder format means leagues can accommodate all skill levels (whether you're way better, or way worser than everyone 🤪).

    Everyone is welcome, whether you’ve never played or are more advanced!

  • Socials & Happy Hours

    Every league has their own happy hours and socials throughout! 🍻

    When we say the world's funnest league, we mean it...on and off the courts.

Welcome to our hometown city... Chicago, where Silly Pickles began 🤠 (also home to our first-ever LGBTQ+ leagues 🌈)

Since our start, we’ve been bringing the same energy to every single week. We handle the matchups at your level, the structure, the happy hours, and the off-court hangs so you can focus on showing up, playing, and actually meeting new friends.

In our leagues, expect consistent games, new matchups, and a super social atmosphere that makes it easy to jump right in 🤪 Chicago's also home to our first-ever LGBTQ+ leagues 🌈

Whether you’ve never picked up a paddle or you somehow own four already 👀 you’ll be paired with players at your level with our ladder format.
No matter your level, come bring your A-game. Or don’t 😜 Either way, we hope to see you on the court 🔥

LEAGUE FAQS

Do I need previous league experience to join?

Nope! All of our leagues include a beginner intro session, so we'll teach you the basics!

Most players are newer to pickleball, and our league generally, so you'll fit right in! Our ladder structure always keeps you playing at your level, even if you get really good, really quick 😉
Can I request to play with a friend?

Our leagues are intentionally designed for social play, so we can't guarantee that you'll be placed with your friend during games.

You may end up on the same courts if you're the same level, or come early / hang late with them to socialize!
How does the ladder format work?

Each week, you’ll be placed in a group with players close to your skill level. You’ll play mini games to 15, rotating partners each round.

When you’re done, submit your scores. From there, you'll either stay in your current group or move up / down the ladder for the following week.
Do you offer refunds if my schedule changes?

Before the league starts, we can definitely work something out! We know life happens. We are not able to provide refunds for individual nights missed.

If Silly Pickles need to reschedule for a week for weather or a facility-specific event, we'll let you know ahead of time and either have a make up session, or refund you for that game day!
Do I need to know all the rules before playing?

Not at all! We also offer intro sessions for new players who want a quick walkthrough before jumping into league play. Pickleball rules are easy to pick up as you play, and our hosts are always happy to help with questions.
Can I stay and hang out after my session?

Definitely! Half of our fun happens off the courts. Many of the venues we play at have social areas where players like to gather before and after matches.

Grab a drink or a quick snack, relax, and stick around to watch other games. We'll also have some planned league get togethers for you! Check your group chat for an invite!