I’m in just as much disbelief as the rest of you that it’s already the first weekend of December. Somehow, we blinked and the entire fall season fast-forwarded straight into twinkle lights and holiday chaos.

And even one week in, the holiday stress is creeping in - like that paleo eggnog creamer that somehow ends up in your cart every year, even though it’s never actually good, but you convince yourself it’s festive. So I am daily reminding myself to slow down and actually enjoy this season of life—one that’s hard and busy and overwhelming, but also completely magical.

Chicago has so many holiday events, and I’m always trying to sort out what’s actually special versus what feels like a grifty pop-up. (You can see my curated holiday weekend itinerary here.) This year we added a few new traditions: Morton Arboretum Lights—which completely exceeded expectations and was short, sweet, and perfect for littles—and a trip to historic Long Grove for their tree-lighting festival. We also kicked off the season at our favorite neighborhood pizza spot, which transforms into Little Nero’s for the holidays.

Like so many parents, I feel the pressure to make every moment Instagram-worthy—to collect as many sparkly “core memories” as possible. But the truth is, my kids mostly want one thing: our undivided attention with our phones put away. So that’s the tradition I’m committing to. No matter how many holiday events we check off, each kid gets a 1:1 parent date. I’m already excited to see what they choose each year.

For now, I’ve planned “mom and me” dates based on what I know they’ll actually enjoy—letting myself off the hook for things that aren’t right for this season. My first grader and I are going to the Nutcracker and then to a festive dinner at JoJo’s Shake Bar. With my three-year-old, we’re heading to the North Shore for the Town & Oak Home Alone popup (our kids discovered the movies this year and are obsessed) and then up to Lake Forest for a holiday craft workshop at Lucy & Lolly’s Whimsy Workshop.

We also just got back from Thanksgiving in Kohler, Wisconsin—our first time not hosting in our home. I had mixed feelings going into it, but I was honestly surprised by how much we loved it. I’m sharing my full (and completely honest) review below.

Finally, for those of you who’ve been here from the beginning—thank you. I started this newsletter last January on a whim. I love my full-time corporate job, but I missed being creative and kept feeling that little nudge to “just try it.” I told myself I’d give it one year, and while we’re still a small but mighty community, I’m incredibly proud to have highlighted so many local Chicago businesses—including 10 female-owned small businesses. Meeting many of these women IRL has been the most rewarding part of building this scrappy little newsletter. I’ve recapped all 10 in this final 2025 edition and can’t wait to spotlight even more in 2026.

🙋‍♀️ If you’d like your business to be featured in a future issue in 2026, just reply to this email!

For those who are new here (probably thanks to the Little Nero’s pizza reel 😜)—welcome! Each month, I share fun things I find around the internet, helpful links, and kid-friendly happenings in and around Chicago. Your support means the world, and if you know someone who’d love this in their inbox, feel free to share the link below.

🖼 Ornament Frame: I turn our favorite holiday photo into a Framebridge ornament every year, and I love pulling them out when we decorate the tree. They also make a perfect grandparent gift.

📸 Christmas Card Book: I bought this Christmas card book last year, and it’s such an easy way to archive our Christmas cards with little notes about the day or the photo shoot. It becomes a sweet keepsake to look back on each season.

💚 💗 Lola and the Boys Wicked Collection: Lola and the Boys sent me the cutest lounge sets from their new Wicked collection, and they’re going under the tree for the Broadway lovers in my life (myself included). Perfect for cozy movie nights.

🧇 Holiday Waffle Maker: The best $10 I’ve ever spent. This mini waffle maker is fast, low-mess, tiny enough to live in any drawer, and makes the cutest little waffles.

🛷 Funboy Snowmobile Sled: I don’t love the cold, but I do love feeling like we’re living inside a snow globe right now. These Funboy sleds are on my gift guide—they’re big enough for the whole family—and I’m also eyeing their holiday inflatable beds for cozy movie nights and sleepovers.

🤎 Melissa Fur Clogs: I’ve always loved Mini Melissa for my girls, but never shopped the adult line until now. They sent me a gifted pair of platform fur clogs, and I’m obsessed. They’re completely waterproof, so perfect for slipping on to run errands in this weather.

❄ Light up snowfakes: TikTok got me. I ordered the viral paper snowflakes for our playroom and have zero regrets—they’re whimsical, sweet, and surprisingly easy to assemble.

🧱 LEGO Ornaments: I grabbed these LEGO ornaments at Target as a fun craft for my LEGO-loving crew. A follower pointed out they’re also perfect for holiday party favor bags and classroom gifts since they come in packs of four—genius.

With our kids off for a full week over Thanksgiving and only three grandparents planning to visit, my husband and I decided to skip the cooking, cleanup, and inevitable mountain of leftovers and plan a family getaway instead. We looked at everything—from the Caribbean and Florida to drivable Midwest towns—but ultimately decided that with a napping three-year-old, something close-ish to home (but still fun) was the smartest move.

This was our second family trip to Kohler. We first visited in 2022 while our upstairs was being renovated, and we stayed for an extended weekend with a then–3-year-old and 1-year-old… which, in hindsight, was a little unhinged. We basically rotated between the resort gym, the pool, and our room, and I’m still not entirely sure why I landed on Kohler other than the fact that I was knee-deep in a bathroom remodel and the algorithm must have been feeding me nonstop “Kohler everything.”

This time, though, I came in slightly more prepared—and bringing grandparents along made the trip infinitely easier and more enjoyable.

We stayed at the Inn at Woodlake, which I’d describe as the “business casual” cousin of The American Club. I initially booked the American Club because I can’t resist a boogie hotel experience, but ultimately switched to the Inn for a bigger suite setup that connected with the grandparents’ room. It ended up being the right call for accommodating our energetic 3- and 6-year-olds who have not yet mastered the art of a hotel chill.

🚐 The Kohler Shuttle (shockingly, the star of the weekend)
I know it sounds dramatic to rank the shuttle as the #1 highlight, but it was life-changing. A lovely sprinter van picked us up anytime, anywhere—American Club, the Inn, Thanksgiving dinner at Blackwolf Run, the indoor pool. We never waited more than 2–3 minutes, and not having to do the winter-gear car seat shuffle was chef’s kiss. The kids thought riding in it was the height of luxury.

🥐 Free Breakfast at the Inn
Simple but solid, and so helpful when traveling with kids who wake up ready to eat immediately.

🏊‍♂ Sport Core Gym + Indoor Pool Access
Great facilities—clean, big, and with plenty of options for getting wiggles out.

🧘 Free Yoga + Spin Studio Classes
A very welcome break for parents who need a moment of sanity.

🎄 Holiday Events
Before we visited, Kohler posted a calendar of events for the weekend including gingerbread-making classes at the American Club with a professional chef (this was a trip highlight), reindeer visits, Santa meet-and-greets, tree lighting, and family nights at local restaurants. It felt festive without being overwhelming.

🍽️ Great Restaurants
Taverne on Woodlake, Horse & Plow, and the Greenhouse Cafe were all hits for both kids and adults.

🚗 Close to Sheboygan
A cute little town, 10 minutes from Kohler if you want a change of scenery or additional dining options, and they have a great children’s museum we visited on our first day.

😊 Friendly, Warm Service
Every single person we encountered was kind, patient, and so sweet to our kids.

The Inn at Woodlake is pleasant—but very no-frills: Clean, comfortable, functional. But don’t expect American Club ambiance.

Limited lunch options:
Breakfast and dinner were great, but midday choices felt sparse if you’re staying put with young kids.

The spa has a two-treatment minimum on weekends/holidays:
Being so close to the Spa was a bit of a tease, and the booking rules make it harder to pop in for a quick massage or treatment unless you’re ready to commit time and $$$ on a family trip.

Overall, it was a net positive experience, and even though my next trip will absolutely be sans kids so I can take advantage of the spa, we would definitely go back as a family, especially when they have special programming. Kohler would also be a fun weekend trip over winter break while they have their Frozen Fairways, which includes ice skating, curling, and winter activities.

🚃 Fannie May Jolly Trolley
A free, festive ride on a vintage trolley that loops down Michigan Ave with four stops—each featuring a signature Fannie May chocolate. I got to preview this last week and it was super cute. This event was so popular that the reserved tickets are sold out, but you can try to walk on at any of the route stops if you are bopping around downtown.

🎭 Rudolph Runs Wild (The Second City)
A goofy, high-energy Second City kids production that puts a hilarious twist on the classic Rudolph story. Fast-paced, funny, and perfect for younger audiences.

🎻 The Holiday at the Symphony Orchestra
A magical CSO holiday performance of the beloved Christmas movie - great for date night, moms’ night out, but also still family-friendly.

🍕 Home Alone Suite at Graduate Evanston
A fully themed Home Alone hotel room complete with cheeky references, photo ops, and 90s nostalgia. A must for little Kevin McCallisters-in-training.

🧊 Illumidomes at Morton Arboretum
Cozy, heated geodesic domes with views of the illuminated forest—an elevated, calm way to experience the Arboretum lights with kids in tow.

So honored to have met and worked with this incredible group of female business owners. Below is the list of women-led businesses I highlighted this year—talented experts (and all Chicago moms!) who can help with just about everything, from gelato to life insurance!

👶 Co-working space with childcare:
Le Village

👪 Life Insurance: Elana Cepa aka The Life Lady

👕 Custom apparel printing: Lemolade

📸 Heirloom black and white family portraits: Bridget Matkovich

🤰 A village for new moms: Mama League North Shore

🍨 Delicious gelato and coffee: Cafe Castemilla

🀄 Learn to play Mahjong: North Shore Mahjong

🧖‍♀️ A relaxing mom’s only retreat: Restorative Reset

Maternal and post-partum support: Maternal Sunshine

Delicious small-batch sourdough: Windy City Sourdough

Want to promote your business in the next Funletter? Respond to this Email with your business inquiry, and let’s chat! 💖

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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