Hello Spooky Season!

It’s finally cooling off in Chicago, and the best season is upon us. I live for Fall weather in the Midwest, and finally ready to hit up a pumpkin patch or Fall fest now that it’s not a sweltering 90 degrees. 🥵

I know this is the time of year when parenting chaos is at an all-time high. You’re scrambling to dig Halloween decorations out of the basement while simultaneously ordering Christmas pajamas because they are on sale - oh and don’t forget there is another other holiday or 2 sprinkled in, so make sure you have every, single, one of those days filled with a fun and engaging activity! 🫠 But also practice self-care! Make sure to carve in “me time” to lift those weights, meditate, deep breathe, use an infrared sauna, hit your protein goals, and finally sign up for reformer pilates class.

While I don’t have any groundbreaking tips for managing these months of maheym, I am going to simply try to enjoy it. I am embarrassingly behind on curating my family photos into prints and albums. (Confession: I FINALLY printed my 6-year-old’s first-year baby book 5 years later) which felt amazing to check off my list - truly can’t believe I put it off that long - but as I was going through our first Halloween and first fall photos, I was reminded how magical this time of year can be with little ones amidst the chaos. In the spirit of FUN my Top 8 is some fun, seasonal toys and activities for kids of all ages that could come in handy on some of those out of school days.

Speaking of photos, I know family photo sessions are in full swing—and if there’s one thing I’ve learned over the years, it’s this: figure out YOUR outfit first and then plan your kids and significant other accordingly.

Last year, I made the mistake of lining up everyone’s outfit but mine and found myself panicking in a Nordstrom dressing room mere hours before the shoot (do not recommend). So this year, I’m learning my lesson and nailing my look first—probably with this blouse or this dress.

I’ve been so lucky to work with some amazing Chicago photographers who’ve captured our family through the years. Here’s a roundup of the ones we’ve used—and honestly, they’re some of the best in the city!

If you haven’t booked your holiday photos yet, check their websites below for Holiday mini availability.

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.

🧡 Life of a Showgirl Hoodie (local biz find!): One of my favorite kids’ brands Lola and the Boys (created by a Chicago mom!) is known for their bejeweled Swiftie sweats and their latest drop for the Life of a Showgirl album - including sweatshirt and PJs - would be a great way to check an item off your Xmas list for the Swiftie in your life.

🛀 Spooky Bath Bombs: Sweet Bath Co has an awesome collection of Halloween bath bombs, including a K Pop Demon Hunters collection. I like supporting this brand since it’s female-owned, employs fellow moms and the ingredients are all-natural.

👻 Halloween Sensory Dough Kits: Another female-owned small business, Young, Wild & Friedman creates sensory dough and slime kits in adorable Halloween themes, available in a range of sizes to spark creativity and play.

🌈 Mess-Free Rainbow Drawing Pads: I keep these scratch drawing pads in my purse to have handy in restaurants - my kids love them, and they come in bulk packs with Halloween and Christmas themes so they are great for classroom parties or birthday party favors.

🎃 Unique Halloween Party Supplies: If you're hosting a Halloween party this year one of my favorite party supply companies, Bonjour Fete, has a great selection of unique and stylish Halloween party decor - love their Wicked collection. They also have a curated page for building “Boo Baskets,” which are all over social media right now.

🩲 Creepy Pair of Underwear Book: A favorite in our house - the tale of Jasper Rabbit and his creepy underwear is a super cute and funny children’s book perfect for this time of year. It’s the first of a series with Creepy Carrots and Creepy Crayons!

🧙 Potion Necklace Kit: I’ve yet to encounter a child who doesn’t love “making potions,” and this kit from Super Smalls seems like a slightly more mess-free way to let them be creative and keep their creation as a fun piece of jewelry.

💀 Viral Skeleton Earrings: These sell out almost every year, and J.Crew Factory has an identical pair to the popular pricier set for only $14.

Bobbety Magazine - Bobbety® is a fully-illustrated, ad-free, quarterly magazine for kids to learn fun facts about science, history, culture, and engage in art and games. The design is SO fun - and both my kids love flipping through the colorful pages.

The Magic Playbook - The ladies behind the popular activity book subscriptions (which we love in our house) launched a Kickstarter for a monthly magazine and you can still support their kickstarter and subscribe for a 3,6, or 12 mo subscription.

Lego Magazine - Lego’s magazine is FREE and great for kids 5-9 years old and sent out 5x a year.

The Journal of Nonsense - If MAD Magazine was made for kids - each issue of The Journal of Nonsense delivers offbeat activities, goofy jokes, and playful games that spark imagination. Recommended for ages 6-13.

🎃🎄 Nightmare Before Christmas restaurant pop-up - River North
If your kids are fans of the Tim Burton cult-classic movie (mine are obsessed) Treehouse in River North has transformed into the movie’s whimsical world, filled with glowing pumpkins, fun decorations, and a themed menu. The bar/restaurant is family-friendly before 8 PM. Reserve on OpenTable

☕🍁 October Cafe - Norwood Park
October Café brings cozy fall vibes year‑round but this month is the perfect time to visit. This family-friendly cafe is known for creative coffee flights, GF and vegan treats, and a cute merch corner—an easy stop off near the Metra in Norwood Park.

👻🍦 Chocolate Shoppe Ice Cream - Edgebrook
I have no other way to describe this place other than it’s fun, spooky, a little creepy 😛 and definitely gives off fun Halloween vibes served alongside delicious ice cream and treats.

All Month: 👻 Haunted Hues at Color Factory

All Month: 🦓 Boo at the Zoo (Brookfield) - Tuesdays / Thursdays FREE days in October and November

All Month: 🍁 Fall Fest @ LP Zoo

Through Oct 19 📖 Mo Willems Elephant and Piggie @ Greenhouse Theatre

Through Oct 19 🦁 Lion King @ CIBC Theatre

Oct 11 - Jan 🐠 Finding Nemo @ Marriott Theatre

Oct 13 - Free Day @ Chicago Botanic Garden

Oct 18 - 🧙 Arts of the Dark Parade (State Street)

Oct 18 🐶 Paw Patrol opens at CAMP

October 25 🍂 Elawa Farm Fall Fest (Lake Forest)

October 25 Slightly Spooky Saturday @ Navy Pier

October 25 Kid’s Monster Mash @ Rooftop Cinema Club - Silent disco dance party followed by showing of Hotel Transylvania

Nov 2 Tuff Taylor with Rod at the Tuffcurls @ Joe’s Live Rosemont A live-band Taylor Swift tribute with bracelet making stations.

Through Nov 9 📦 FORTS! Build Your Own Adventure Using cardboard boxes, sheets, clotheslines and more, an interactive theatre experience where you build your own amazing adventures.

Through Nov 16: 🐭 Leo Lionni’s Frederick @ Chicago Children’s Theatre

Windy City Sourdough is a local cottage bakery run by Maggie, a former teacher and mom of three who turned a baking hobby for hungry neighbors into a full‑blown business thanks to huge demand for her amazing bread!

Each week she releases a new lineup of small-batch and delicious loaves—think pumpkin cinnamon swirl focaccia and s’mores sourdough—that sell out fast!

Every loaf also gives back: $1 is donated to the DDx3x Foundation in honor of Maggie’s daughter, diagnosed in 2022.

Follow Maggie’s weekly sourdough and bread drops with pickup dates (they sell out fast!) on her Instagram at @windycitysourdough.

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!

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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