🦁 Welcome Leo Season!

July certainly was a whirlwind over here - between the 4th, work trips, family vacations, big birthdays, and a lovely cold virus that took us all down - part of me is ready for the routines of back to school, while the other part is panicking that summer is almost over.

This summer, it felt like everyone was either in Europe, at the Sphere, or checking off amazing adventures from their bucket lists. And while I wasn’t jetting first class to those dreamy playgrounds in Switzerland that won’t get off my Insta feed, I did do more fun outings and trips than in years past—and felt so privileged to do so.

But I wanted to quickly acknowledge that if you just started following along with me, it wasn’t always fun-filled “big weekends” all the time. This time last summer, I had a kid still in diapers with a rigid nap schedule, my mom was recovering from major, scary surgery, and we were trying to juggle and budget childcare for yet another year of soul-crushing daycare bills. I remember feeling so crestfallen by the end of summer when we had made it to the community pool maybe three times, and I felt like I was failing as a mom.

If you are in this season of life—either with a baby, an ill parent, or dealing with something that makes big summer plans impossible—I see you, and I’ve been there. This summer truly felt like the first time I could see a glimmer of what all the other moms on social media meant when they were YOLO-ing on summer break. Life circumstances and my kids getting older certainly helped.

And if you’re reading this sitting in a dark room with the sound machine blasting, alone in a nursery while everyone socializes outside—just know that we’ve all been there. And I can truly say it makes the moments where you look around and are actually enjoying summer with your kids even sweeter. It’s annoying when everyone says it, but it WILL get easier.

Also, I highly recommend going back through your photos from this summer—you probably did SO much more than you think! If you still want to check some “summery” things off your list, I made a quick end-of-summer bucket list for some last-minute activities.

And while we are still planning those last-minute summer memories, the school emails have already started coming! I am trying to be a little more prepared than I was last year, so I’ve already started to do some back-to-school shopping, and I’m sharing some of my finds in my Top 8. Plus, as a thank you for being a reader, I made a free printable for your first day of school pics! 📷

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.

🍱 A Fancy Bento Box: Is your kid even Gen Alpha if they don’t have a climate-controlled, BPA-free, colorful bento lunch box? I crowdsourced the best from moms on Instagram, and the top-voted were the Omiebox, the Bentgo chill, and this budget-friendly stainless steel one from Target.

🧦 Socks for kids who hate socks: If this is your kid - you know how unhinged the morning routine is for kids who hate socks or have sensory issues. This sock nightmare plagued both my kids, and even though I tried all the “seamless” and “sensory friendly” pairs from Amazon, these light-weight Bombas are the only ones they will wear. They have them for bigger kids as well. Do I die a little paying $50 for socks - yes - but it’s also completely worth avoiding the meltdowns when trying to get out the door. (If you’re not convinced, most of the 5-star reviews are from parents with sock PTSD)

✨ DIY Backpack Charm Kit: While maybe not as exciting as a rare Labubu, we made bag charms for my daughter’s 6th birthday party activity, and it was a hit. If you need something to do on those endless few days before school when you have no camps and your babysitters are back in school, this bag charm kit would be perfect to whip out. (PS Everything right now on baublebar.com is 25 off%)

✏️ Pencil Confetti Poppers: Packed Party has a really fun back-to-school collection, and these pencil confetti poppers would be cute for back-to-school pictures.

🍁 2-in-1 Fall Jacket: I pretty much always have something Mini Boden in my cart, and I especially love their fleeces and jackets for back-to-school shopping. They hold up great for hand-me-downs and these 2-in-1 jackets for girls and guys are great for our chaotic weather.

🧳 Activity Duffel Bag: Crate and Kids has a great back-to-school collection (and on major sale), and this personalized duffel bag in fun colors looks perfect for after-school activities, weekend trips, or sleepovers.

💤 Back-to-school pajamas: Gap has a huge sale on pajamas right now and these back-to-school prints are super cute and only $12.

☎️ Tin Can Phone: I first spotted this brand thanks to Katie Cassman (if you live on or frequent the North Shore sign up for her newsletter!) Created by a group of Gen X and Millennial dads, it’s basically a landline for kids—programmed by mom and dad—so they can call just their friends and family. While the idea makes me want to face-palm a little, I’m fully here for our kids embracing analog life—even if it means repackaging something totally ordinary from our childhood into something kitschy and cool.

If you feel like summer snuck by without as many activities as you planned, here are a few ways to check off those bucket list staples.

📽️ Enjoy an Outdoor Movie
There are still movies on the schedule for the city and most burbs, including at Oakbrook Mall with outdoor movies every Wednesday until the end of August. If the park isn’t your jam, this viral projector that syncs with your streaming apps makes it look super easy to set up a movie outdoors.

🏕️ Make (or just eat!) s’mores
Or if you can’t make it to a bonfire, Little Goat dinner has a summertime s’mores sundae and kids eat free on Tuesdays from 4-7 PM.

🫐Make a farmers market dessert
Every summer, I make this lemon zucchini blueberry cake from Ambitious Kitchen, from fresh produce, and it’s on my list for August.

🔭 Check off a Museum Visit
Adler Planetarium offers Free admission for Illinois residents every Wednesday evening from 4–10 p.m. and it’s the perfect spot to grab sunset skyline view pictures.

🍦 Try a fun new ice cream spot
Megan, aka mamaknowschicago, shared an awesome roundup of adorable animal—themed ice cream around the city if you want to venture out from your local ice cream spot.

Ends this weekend: 🎭 Arthur and Friends

Through August 👾 Arcade Exhibit @ Elk Grove Village library

Aug 9 🪕 Laurie Berkner @ Ravinia

Aug 10 🐛 Bugapalooza @ Petty Notebaert Nature Musuem

Aug 11 🎶 Broadway Night @ Pritzker Pavilion

Aug 15 🚜 Evenings on the Farm @ Wagner Farm

Aug 16-17 🪂 Air and Water Show

Aug 16-17 🖼️ Evanston Art & Big Fork Festival

Aug 22-24 🫒 Taste of Greektown

Aug 23-24 🏀 Bulls Fest @ United Center

Aug 26 🩵 Chicago Sky Night @ White Sox

Aug 29 🐊 After the Age of Dinosaurs opens @ Field Museum

Sept 2-3 🌭 School night special @ Chicago Cubs

Maddie was one of the very first connections I made in my community after starting this newsletter, and I was instantly drawn to her warmth and genuine spirit. A Park Ridge mom to an adventurous two-and-a-half-year-old, she knows firsthand how challenging early motherhood can be. Despite having a healthy pregnancy, a strong support system, and 12 weeks of paid leave, Maddie experienced severe Perinatal Mood and Anxiety Disorders (PMADs)—the darkest season of her life.

Out of that experience came Maternal Sunshine, Maddie’s mission to connect families with the perinatal resources that are out there, but often hard to find. She hosts community events for Chicago area families to foster postpartum support and now offers in-home postpartum doula services—meeting moms exactly where they are, with understanding, empathy, and light. Make sure to follow her on Insta for the latest events and meetups.

Maternal Sunshine Upcoming Events:

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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 September 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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