Naperville, IL: Pickleball Ladder League at The Picklr | Summer 2026

Regular price: $158.00
Regular price
Sale price: $158.00

Hey Naperville, we're back! Hope your paddle's warmed up 😉

📍 Location: The Picklr - 740 Illinois Rte. 59, Naperville, IL 60540

📅 Schedule: 8 Weeks of Play
Start Date: 07/19/2026
End Date: 09/13/2026 (Skipping 09/06)

⏱ Timing: 1-5pm on Sundays. You'll play one full hour each week. Time slots rotate weekly (1-2pm, 2-3pm, etc).

🏓 Real Reviews From Real Pickles

Making new friends in your 30s isn't exactly something that happens every day, but Silly Pickles somehow makes it feel easy. I'm on my 5th season, and I absolutely love it!!!!
Chicago, IL
I've played in a lot of adult rec leagues over the years, and Silly Pickles is my favorite by a longgggg shot. I'm a lifer!

Philadelphia, PA
This is the best pickleball league in all the land!! It's very organized and makes it so easy to join, learn, and gain some life long pickle friends!
Houston, TX
I joined a league and had the best time! Silly pickles is so much fun and a great way to meet people!
Orlando, FL
Sooooooooooooooooo much fun. I don’t regret it. It’s a lovely way to spend a Sunday afternoon/evening. The place that my league plays at is amazing. It’s got like 30 courts, indoor, outdoor. There’s a bar, burger stand and a restaurant. This was my first time playing pickleball. I saw an Instagram ad and signed up for the fall league. I liked it so much. I signed up for summer immediately after.
Raleigh, NC
Silly Pickles is a fun way to play pickleball. The league matches players of similar skill levels, making games enjoyable and welcoming. The happy hours are also fun after the games. Highly recommend!
Miami, FL
I’ve really enjoyed the Atlanta Silly Pickles league! I love the ladder play and how you don’t have to have a partner, but you get to meet three new people each week!! This league is awesome for every level of player and it’s been great for me as a beginner!
Atlanta, GA
What really sets Silly Pickles apart is the community. The happy hours and social vibe mean you're constantly meeting like-minded people who want to play hard, laugh a lot, and actually make new friends.
Boise, ID

1 8

🤠 How it works:

Game Day
Each week, you'll have one hour of scheduled play within a new group of four, for 2v2 doubles games.

Rotate partners each game, so say hello to new friends and friendly competition every week!

*The only thing you need to bring is a paddle.
Always Play at Your Level
All skill levels are welcome! 🚀 Total beginners to DUPR 4.0 legends, we'll match you at your level with other players every week.

All leagues come with beginner support, so you can learn the basics and jump right in!
The Ladder Format
Each game day, you will play with different people at your skill level, which is less intimidating for our beginner pickles, and more fun for our advanced pickles!

You'll enter your scores after games, which we use to move you up or down the "ladder" - so you play at the right level week to week.
Can't Make A Week?
No worries! Each week we'll request your RSVP, so we can make accurate schedules for the week ahead.

Simply reply 'no' and we won't put you in the schedule 📅 Your rank may change slightly, but nothing major while you're out!
Meet New Friends
In addition to league play, every season has planned socials! Given you only play with people at your skill level, this is a great way to meet players that are way better than you (or way worser 🤪).

You can sign up with a friend, but everyone plays as an individual with new matchups each week 🍻
Schedule Updates
It’s unlikely, but possible that weather or our facility creates an unforeseen schedule change.

If that happens, we'll do our best to give you advanced notice and shift the date of play. If you can't attend the make up day, we can refund you for that session!

Choose a Skill Level

🤪

Never Played & Uncoordinated

Do you sometimes give baby giraffe vibes? You'll fit right in 🦒
😎

Never Played & Coordinated

You are fairly athletic, just new here! You'll probably move up the ladder quickly once we explain why everyone keeps talking about the kitchen 🥄
🤙

Beginner

You have played a few times, kinda liked it, but are def asking for a friend... how does scoring work again?! 👀
🔥

Beginner-Intermediate

You have the basics down, your confidence is growing, and you’re starting to think you absolutely meant to hit that shot.
🎾

Never Played, Tennis Background

The good news? A lot transfers. The not-so-good news? You may hear “don't swing so hard” a few times. You'll catch on quick!
🚀

Intermediate

Now we’re talking. You rally, compete, and you know showing up without stretching is a dangerous game.

DUPR 3.0 energy 🏆
💪

Intermediate-Advanced

You've got the strategy down, your warm-up routine is getting suspiciously serious, and you def own at least one “lucky” paddle.

DUPR ~3.5 🏅
👑

Advanced

You're progressing to local-league-legend status. Games are getting spicy 🌶️ and we love to cheer them on.

DUPR ~4.0⚡
🎯

Pro

Your paddle has seen things, and people get noticeably quiet when your name’s on the schedule.

~DUPR 4.5+ ✨