Happy September!

I’m officially declaring September “Self-Care September” on behalf of all parents who barely survived the end of summer and the back-to-school whirlwind. Those first few weeks of early mornings, new routines, schedules to sort out, calendar invites, and school emails are not for the weak.

As my reward, I lined up every self-care appointment possible—Botox, a much-needed hair color, nails, and even a workout longer than 25 minutes—just to feel human again. I’ve talked to so many moms doing the same, and if you haven’t yet, consider this your reminder to fill your cup in whatever way feels good.

In that spirit, my Top 8 this month has nothing for the kiddos. It’s all the little things I bought or loved as “Self-Care September” rolled right into “Treat Yo Self September.”

I’m also in full fall/holiday planning mode now, so I thought I’d share a few things helping me stay organized as we juggle back-to-school season.

While a part of me dies a bit spending money on a Christmas event in September…I’ve accepted that this is my fate as a parent in 2025, so here are some holiday tickets already on sale:

Lastly, for those who are new—hello and welcome! Every month, I share a range of fun stuff I find around the internet, helpful links, and things to do in Chicago with kids. You can read all past Funletters here - and your support and sharing of this newsletter means the world! So that I can keep this thing going, if you know someone who would like this email in their inbox, you can share the link below.

🧢 Chic Gingham Hat: I’ve had my eye on Chord hats for a while—I’m always in a baseball cap, and this gingham pattern might finally make me hit purchase. I love that it’s a female-owned small business by Mary Orton, one of my favorite IG follows.

🍂 The Perfect Fall Dress: This Tuckernuck dress is quickly becoming a closet staple. It’s super flattering and comfortable—I’ve dressed it up with heels for dinner and layered it with a turtleneck and boots on a chillier night and it comes in several colors.

✨ Miracle Eye Cream: I’m not a beauty guru—I mostly stick to my dermatologist-approved basics and am pretty skeptical of anything that’s not medical grade. But this Sunday Riley eye brightener actually works. My dark circles look lighter, it has a little glow, and even with no makeup, I feel a little more put together before 8 AM drop-off.

🧥 Floral Barn Coat: The barn coat was huge last fall, and I’m glad it’s sticking around since it’s such a classic look. Tuckernuck’s new collab with Barbour is super feminine and cool—and in Chicago, there’s no such thing as too much outerwear. I don’t make the rules. 🤷‍♀

🍁 Quiet Luxury Tote: This brown suede tote was my first accessory purchase from Quince and truthfully, I was blown away at the quality. It’s way roomier than it looks - it fits a laptop, personal belongings and alll the snacks + kids stuff and is under $200.

🐆 Leopard Sneakers. I could not resist these leopard Adidas with the bright orange laces - they’re fun and super comfortable, and I promise you will get compliments on them wherever you wear them.

💤 Cozy Rugby Shirt: To the delight of my inner middle-school self, rugby shirts are back! I found this oversized / sweatshirt-style, which is perfect to throw over jeans or leggings, and you may even impress the Gen Z kid in your life (but unlikely).

🍹 THC/CBD mocktail mixer: This month, I shared in my Instagram stories that I passed my 2-year no-alcohol milestone 🥳 so when I want to imbibe in something other than sparkling water, I’ve turned to low-dose THC and CBD drinks. One of my favorite brands Cann, now has an unflavored and zero-calorie on-the-go mixer you can pack in your purse to make any mocktail a little more exciting.

“Treat Yourself” month continues—I’ve been lining up babysitters and sneaking in a little fun to our busy weekends.

🧑‍✈ Travel back in time with a retro dinner and a show
Start with a classic steak dinner at Wildfire (It’s scratch-off time at Lettuce Entertain You Restaurants), then head down the road to the Marriott Theatre for Catch Me If You Can. Broadway favorite JJ Neimann absolutely shines—it’s honestly one of the best shows I’ve seen in years. Plus, there’s not a bad seat in the house.

🌙 Outdoor Movie Night
Take advantage of these warm fall evenings with a classic movie and the city as your backdrop at Rooftop Cinema Club. Make it a full night out with dinner at Rose Mary (one of my personal faves) or pre-show cocktails at TimeOut Market.

You may know of the big Fall fests like Bengtson’s or Goebberts but these smaller spots are my favorites that we have visited and still deliver pumpkins, cider, activities for little ones and a close parking spot. 😉

🎡 Sonny Acres Farm – West Chicago
Sept 20 - October 30 - Family-run with pumpkins, a mini carnival, pony rides, petting zoo, and cider donuts. Pro tip: the crowds die down in late October.

🎃 Didier Farms – Lincolnshire
Sept 18 - October 26 - Classic fall fest with pumpkins, corn maze, kiddie train, and roasted corn. Easy, local, and family-friendly.

🐴 Johansen Farms – Bolingbrook
Sept 14 – Oct 31 — A sweet, kid-first farm that’s smaller scale but still has lots of activities — about 35 minutes from the city.

Through Sept ⌛ Escape the Museum at MSI (after-hours escape room exhibition for ages 8+ is back with more dates after selling out last year.

All Month: 👻 Haunted Hues at Color Factory

Sept 13-14 🧑‍🎨 Ravenswood Art Walk

Sept 13 & 27 🧑‍🌾 North Branch Farmers Market (The original kid-friendly market)

Sept 19 🪩 80s vs 90s Night at the Zoo (Adults Only Evening at Lincoln Park Zoo)

Sept 20-21 🎨 West Loop Art Fest (family friendly)

Sept 19-21 🥨 Oktoberfest with the Cubs

Sept 26-28 🍎 Long Grove Apple Fest

Sept 26 - Oct 26 🦁 Fall Fest at LP Zoo

Sept 27 🎉 Hispanic Heritage Fest @ Brookfield Zoo

Sept 27 - Oct 19 📖 Mo Willems Elephant and Piggie @ Greenhouse Theatre

Sept 28 - 🎟 Kid’s Free Day @ Chicago Children’s Museum

We all have a closet full of T-shirts, but how many do you actually reach for because they’re soft, cozy, and easy to style? That’s exactly what Nikki and Morgan (fellow Chicago moms) set out to create when they started Lemolade—tees and sweatshirts that look cute, are comfortable, and show off community pride. Their collections include Chicago-inspired designs, playful kids’ lines, and community pride.

They also offer custom design and print services if your school, business, or organization needs apparel with heart (and comfort) behind it.

Supporting female-owned businesses like Lemolade is a good reminder of why it’s important to support local —their Lemons to Lemolade line is all about giving back. Throughout the year, they release limited-edition designs that shine a light on organizations embracing optimism and positivity—and to date, they’ve donated over $55,000 to these amazing causes.

Just for Big Weekend subscribers, use code BIG15 for 15% off your order on shoplemolade.com or mention this newsletter when you place a custom design order for a waived design fee! 🎉 For custom orders, Email [email protected].

Want to promote your business in the next Funletter? Respond to this Email with your business inquiry.💖

If you want even more Big Weekend content, follow me on Instagram where I will share more content and resources like this, and be sure to tag me if you find yourself doing any activities from this list! If you know someone in your network who would like this content, you can forward this email or have them subscribe here.

Keep an eye on your inbox in October for the next Funletter - I aim to send these out at the beginning of every month.

P.S. While I do my best to highlight as much as possible, I may miss an event or two (or have a typo or three) since I am a one-woman show.💃

Feel free to send me any leads or ideas for future Funletters by replying to this email.

XOX

💌 Kaitlyn

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