This week officially marks one year(!) since I started this newsletter and this past week I have forced myself to reread my first sends and look at some of my first reels I started creating. Even with years of experience doing graphic design, content strategy and dabbling in content creation I am still surprised by how much I have learned from this experience from a friend casually saying “you should send a newsletter or something”.

So if you’re reading this and you have that nagging feeling you can’t shake that you want to start something - your own business, an instagram creator account (yes there are tons but there is only one YOU with your POV) then this should be your nudge to just do it. While juggling a full-time job and motherhood, I definitely asked myself once or twice this year, “Why the heck am I doing this?” But seeing myself grow (cringe first reels and all 🫣), discovering new parts of Chicago with my kids, and connecting with other local moms - that I never would have met without a fun little Instagram newsletter account - was such an additive aspect of my year. 💗

This newsletter has also pushed me to explore experiences around Chicago I probably wouldn’t have tried otherwise — all thanks to a little accountability from running an account about having fun. Some favorites from the past year: art classes at Lucy and Lolly, the Ryan Learning Center at the Art Institute, our long weekend in Milwaukee, first Vintage Fireboat Cruise, and making pottery with my daughter at MADE. This month we’re finally checking out the Sloomoo Institute, Disney on Ice, and the Balloon Museum (discounted tickets linked below!). And as always, if you have a tip or event I should feature, I love getting emails and DMs!

I’m also sharing what I packed for a three-day Disneyland trip — with a full recap coming later this month — plus road trip ideas for January–March long weekends and ways to thrive (not just survive) Chicago winter with kids. And as I kick off year two of highlighting female-owned businesses, be sure to scroll to the end for a free home evaluation from local realtor Jackie Merlo in this month’s Small Business Spotlight.

A new year always feels like an invitation to try, explore, and say yes to more fun—and that’s exactly the energy I’m bringing into 2026. Thanks for being here as we kick it off together and I hope it continues to be a bright spot of content in your inbox.❣

👟 Comfortable Shoes: However much you think you will walk at Disney, double it and then add some more. A coworker told me about these Air Max platforms that she traveled all over Europe in, and I can confirm they are great walking shoes. The platform makes them cute with either jeans or leggings.

☔ Warmish layers: Our weather was a mix of rainy and chilly mornings and evenings and warm afternoons so we all had sweaters - I packed this super cute and comfy oversized Minnie sweater for me, Target had cute kid matching sweaters I grabbed for my girls, and we all had raincoats.

👖 Comfy jeans and leggings: These Anthro cropped wide-leg jeans sell out every season for a reason. They are butter-soft and stretchy but still super flattering. I also finally got on the Vuori bandwagon, and I don’t know why I waited so long. Their Daily Form leggings are insanely comfortable with the extra wide waistband.

👝 Varley Belt Bag: We tried to pack for the parks as light as possible - this waterproof Varley belt bag was perfect to keep my phone, wet wipes and Touchland hand sanitizers at the ready and my husband carried a small backpack with snacks, essentials and it was the perfect amount of feeling prepared without lugging too much around.

👸 Monica and Andy Disney Collection: We are huge fans of this local brand and I got so many comments and questions on the princess dresses and my sweatshirt we wore and loved sharing that it was a local Chicago brand. They also have the cutest Cars collection which is SUCH a cool aspect of Disneyland / California and perfect to pack if you visit.

🎀 Personalized Minnie Mouse Ears: Baublebar has a collection of adorable Minnie ears that you can personalize - or Etsy is a great resource for custom ears which is where I found a Descendants pair for my 6-year-old.

😴 Fun PJs: I picked up some new princess jammies on sale from Janie and Jack before the trip but this new line from Posh Peanut is adorable esp for Toy Story fans.

🐭 Classic Mickey Ringer Tee: The best part of Disneyland IMO is all of the retro/nostalgic vibes and Gap has a great classic collection to do a subtle family matching moment. I brought this jean jacket, classic Mickey tee, and Old Navy has cute and affordable looks as well.

We love escaping to Wisconsin for long weekends now that our kids are a bit older. These family-friendly spots—some recommended by friends and some surfaced by the algorithm—are a bit of a drive, but often less crowded than tubing and ski parks closer to Chicago. We are not a ski family so I have bookmarked ideas that offer additional winter activities.

⛸️ The Glide (Boulder Junction, WI) — I saw this on Instagram and it looks SO cool! It’s a free, magical skate through the winter woods on natural ice trails in Wisconsin’s Northwoods and you can rent a nearby cozy cabin.

🛷 Snow Tubing / Ski at Cascade Mountain (Portage, WI) — Kids 12 and under Ski FREE here. Plus they have snow tubing for the entire family.

☃️ Snow Tubing at Sunburst Winter Sports Park (45 min North of Milwaukee) — The world’s largest snow tubing park, featuring 45+ lanes and magic carpet lifts, plus skiing, snowboarding, and cozy food options for warming up. (note: geared toward kids 6 and older)

🎉 Madison Winter Carnival (Madison, WI) — An annual tradition with ice sculptures, outdoor games, live music, and classic winter vibes on the frozen Lake Mendota. 📅 February 5–7, 2026

⛳❄️ Frozen Fairways at Kohler, WI — A uniquely Kohler winter experience that’s surprisingly kid-friendly, with snowshoeing, cross-country skiing, and fat-tire biking—plus an indoor pool, curling, and an ice rink. An easy, cozy winter weekend even with little kids (we went in 2023 and would absolutely go back).

❄️ Ice Bumper Cars at Gallagher Way — A winter favorite outside Wrigley where kids and adults can spin around the ice—no skating skills required - must be ages 7+.

👗 Crafting Character: The Costumes of Paul Tazewell at the Museum of Science and Industry (MSI) — A new exhibit showcasing original costumes and sketches from Broadway and films like Hamilton and Wicked, including Glinda’s pink bubble dress and Elphaba’s Emerald City dress. Opens Jan 19.

🐊 The Enormous Crocodile Musical @ Fine Arts Building — Based on the Roald Dahl classic, ideal for younger theatergoers. Running Jan 29-Feb 21
DISCOUNT CODE: Buy One Ticket, Get One Free with code SNAPUP.

🎈Balloon Museum — I have only heard good things about this immersive experience filled with oversized balloon installations and they are offering a discount through April. Now offering up to 20% off tickets through Bucketlisters.

All Month: 🧱 Homeschool month at Legoland Discovery Center

All Month: 🐾 Paw Patrol Experience @ CAMP Chicago

Jan 19: 🦁 Charlie Harper Exhibit opens @ Chicago Children’s Museum

Jan 19: ☮ MLK Day @ Chicago History Museum

Jan 22-25 & Feb 5-8 👸 Disney On Ice: Jump In @ Allstate Arena
(coming to United Center Feb 12-15)

Jan 23 ⛸ Stranger Things themed Skate night @ Gallagher Way Ice Rink

Jan 23-Feb 28 🥘 Chicago Restaurant Week

Jan 25 🎟 Reduced Price Admission ($5.29) at Chicago Children’s Museum

Jan 31-Feb 1 🎿 Norge Ski Club Annual Winter Ski Jump Tournament: A family-friendly winter fest where you can watch and cheer on athletes from across the U.S.

Jan 30-Feb 1 🧊 Downers Grove Ice Festival

Feb 1 🐶 - Dash and Dance of Lights @ Nature Museum special northern-lights-themed STEM storytime, craft, movement activity, and live science demonstration with children’s author Ashley Key

Starting Feb 5 🎭 Chicago Theatre Week

Sponsored Feature

I’m so excited to share my first female-owned business spotlight of 2026—someone I know through my own community of awesome moms and can personally vouch for as both a skilled realtor and a genuinely lovely human.

A native of the Northwest Suburbs of Chicago, Jackie is a Licensed Real Estate Broker at Compass. As a seasoned real estate agent with years of experience, Jackie prides herself on delivering exceptional service to all of her clients. Her deep knowledge of the local market and her unwavering commitment to personalized attention ensures that you'll receive the guidance and support you need to make the best decisions for your unique situation.


Jackie's interest in real estate began when she sold her two-bedroom condo, and bought her first investment property in Chicago's Roscoe Village neighborhood. There, she learned about the value of owner-occupying an investment home. Since then, Jackie has purchased and renovated three additional properties; a lake home in Twin Lakes, Wisconsin, a 1929 bungalow in Norwood Park, Chicago, and the home where she now lives. Her personal experiences have allowed her to take a hands-on approach with all of her clients, including providing invaluable knowledge about renovation expenses, managing rental properties, and a keen eye for design trends.

Jackie currently resides with her husband, two kids, and beloved rescue dog in a restored bungalow in Park Ridge.

Outside of real estate and managing properties, Jackie can be found traveling, gardening, running, and volunteering at her kids' school. You can learn more about Jackie by checking out her website.

With the Chicago area housing market shifting so much over the past few years, many homeowners are sitting on more equity than they realize. If you're wondering how much your home may be worth today—or simply want clarity heading into 2026—Jackie is happy to prepare a complimentary home valuation report for subscribers. It’s fast, personalized, and far more accurate than any online estimate.

Big Weekend offers paid spotlight opportunities for female-owned small businesses in Chicago and the surrounding suburbs. 💌 Respond to this Email to learn more.

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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