Turning the corner on January in Chicago feels like a mini sigh of relief. I’ve always loved February—it’s short, sweet, and full of little reasons to celebrate: Super Bowl parties, Valentine’s and Galentine’s gatherings, and a perfectly valid excuse to wear red or pink and eat chocolate all month long.

We’re squeezing a lot into this short but packed month, and there’s no shortage of things happening in the city and burbs to keep weekends busy, including Disney On Ice, theater outings like The Enormous Crocodile musical (discount code below—don’t miss it!), and checking out some new indoor play spots popping up in the burbs, including Sip & Play in Park Ridge and The Kid’s Play Hive in Des Plaines.

I’m also sharing a few things that caught my eye that would make fun Valentine’s gifts for kids, significant others, or—highly encouraged—yourself, plus some Olympic-themed activities if your family has Olympic fever like we do (the official posters this year are so cool!)

Expecting parents (or friends of!)—skip to my business spotlight on Expecting Together, a European-style prenatal social club founded in Chicago by local mom Georgia Kastaris. BW subscribers get an exclusive discount to join a neighborhood cohort of fellow soon-to-be parents. I’m genuinely excited to share this because it feels like a potential lifeline for new parents feeling isolated in the city—something I deeply relate to. A village doesn’t magically appear when the baby arrives; you have to build it, and having a built-in community going through the newborn phase together can be game-changing.

As we count down the days until the first day of spring, I hope you find some inspiration to make this month a little more colorful and fun (I think we all could use it) and as always, if you find yourself doing anything you found here please tag me and let me know! Thanks for being here and if you enjoy this content I would so appreciate if you could forward this to a friend who deserves a little fun in their inbox❣

💗 Kiki & Lulu Pajamas: This mom-owned Chicago brand we love just launched a new collection for kids and moms in an adorable, sweet print—perfect for V-day. 100% of sales benefit Penny’s Flight Foundation to help end NF.

🏀 Derrick Rose tee: This month the Bulls retired Derrick Rose’s jersey and did a merch drop with a cool rose-themed tee perfect for a Bulls fan Valentine gift.

🐶 Adopt-A-Pet Valentines: In an effort to cut back on Amazon spending this year and support more local businesses, I turned to Paper Source for classroom Valentine’s including these with a mini animal, bug search and friendship bracelet kit. Also these shipped FAST since they’re local.

🌹 Valentine Jellycat: The hottest gift flying off the shelves is any Jellycat with a hint of red or pink. If you don’t have luck at the Mich Ave Jellycat pop-up, The Paper Store (with a few local locations) had some in stock like this cute rose bouquet.

🖼 Desk Heart Frame: I am finally tackling some empty walls in my house this winter and using Framebridge’s gallery wall design services (will report back) and while browsing the site this cute heart frame caught my eye as a sweet gift.

❤ Cozy red cardigan: I picked up this fun red Tuckernuck cardigan for a Galentine’s event this month but also had my eye on one from Abercrombie and the Sezanne red Gaspard cardigan was calling me but I don’t need 3! (Yes, it’s that good!)

💎 Jeweled kids gloves: Despite my children ONLY knowing life in Midwest weather, it was a constant battle to put on a hat and gloves - until I found the girliest gloves imaginable. These Super Smalls jewel gloves were a hit (we now own 4 pairs) and had to get the matching earmuffs.

💐 Flowers for Dreams Bouquet: This is your sign to order yourself some flowers to celebrate YOU this month! Flowers for Dreams is another local company I love with beautiful artisan bouquets and every bouquet sold benefits a local charity.

While I mostly stick to kid / family content around here I think we can collectively agree that the start of 2026 has been…a lot. February being the month of love is the perfect excuse to schedule a few date nights or ladies nights out - here are a few of my favorite Chicago date nights or ones that came recommended to me by friends.

🪄 Chicago Magic Lounge (Andersonville) — A speakeasy in Andersonville serving craft cocktails and small plates, with magic happening right at your table—strictly 21+. Pair it with dinner at adults-only Hopleaf (order the mussels and a rosé on tap) for the ultimate kid-free night out.

🥃 Drunk Shakespeare (Loop) — An adults-only comedy show where one actor downs shots of whiskey and attempts to perform Shakespeare—while the rest of the cast tries to keep the play on track. Grab dinner before at British pub Monarch and Lion for a cozy English dinner before the show.

🍣 Chopping Block Cooking Class (Lincoln Square) One of my favorite date nights that we do a few times a year - a perfect interactive date night plus a delicious dinner and I always get tons of cooking tips - the hands-on sushi is a great winter activity.

👾 Game night at Elston Electric (Goose Island) This has been on my list to visit for months and an adult-only arcade night (it’s 21+ after 10PM) would be a fun way to end the night after dinner at Goose Island or - nearby Ada Street.

❄️ Après Ski Dinner at Scratchboard Kitchen (Arlington Heights)— Even if you don’t hit the slopes, you can fuel up for a long day of Olympics viewing at Scratchboard Kitchen that has an après ski pop-up through Feb 15. It’s family friendly (with great butter noodles) and do not skip the tabletop s’mores!

🥌 Curling at Kaiser Tiger (West Loop) — Curling at Kaiser Tiger is a surprisingly fun, beginner-friendly winter activity with heated lanes, cozy vibes, and plenty of après-curling drinks - best for families with kids 12 and older. Grab dinner at nearby Macello for a full Milano Olympics themed night out.

⛸ Cozy up in an Igloo (Grant Park) — Show off your skating skills at Maggie Daley Park Skating Ribbon where you can reserve a private igloo to warm up with warm beverages and snacks.

🇺🇸 Olympic Day on Ice (Rosemont) Feb 8 — This Sunday, Rosemont Ice Arena is hosting an Olympic-themed skate with games and contests for ages 5-18.

All Month: 🐾 Paw Patrol Experience @ CAMP Chicago

Feb 5-15 🎭 Chicago Theatre Week

Through Feb 21 🐊 The Enormous Crocodile Musical
(BOGO tickets with code SNAPUP)

Feb 5-8 👸 Disney On Ice: Jump In @ Allstate Arena

Feb 12-15 ⛸ Disney On Ice; Jump In @ United Center

Feb 7 🍦 Jenni’s Ice Cream for Breakfast Day

Feb 7 🍫 Cocoa Crawl Festival in Historic Long Grove

Feb 7/21 ❄ Garfield Park Conservatory Winter Wonderland

Feb 7 - Mar 1 🧝 The Hobbit at Young People’s Theatre of Chicago

Feb 14 💓 MCA Family Day: Heart Strings

Feb 14 - March 8 😺 Pete the Cat @ Big Noise Theatre

Feb 14 🎆 Navy Pier Valentine’s Fireworks

Feb 15 😻 Gabby’s Dollhouse Love @ Rosemont Theatre

Feb 17 🇵🇱 National Paczki Day (where to get them)

Feb 28 🧡 Blippi Live @ Chicago Theatre

Sponsored Feature

I want to start this business spotlight by saying I truly can’t think of anything more important than finding community in the early days of bringing your baby home. Looking back on my first postpartum journey, I’m honestly shocked I made it through—and even decided to do it again! It was lonely, isolating, and made even harder when the pandemic hit while our daughter was just 8 months old. My husband and I very much felt alone on baby island.

It wasn’t until I met another new mom—who had her first baby abroad—that I realized just how different postnatal care and community can look outside the U.S. We live in one of the best big cities with incredible communities, yet so many new parents are still left to figure it out alone. I eventually found my village, but it took time, effort, and intention—and I can’t help but wonder how different those early months would have felt with a built-in community from day one.

That’s why I’m so excited to share Expecting Together, founded by Chicago mom Georgia Kastaris, as this month’s small business spotlight. In the U.S., our medical system focuses on keeping mothers and babies safe—but it was never designed to guide families through the realities of early parenthood. When Georgia found herself pregnant in London in 2023, she discovered prenatal social clubs that paired expert guidance with real connection, bringing parents together by due date, location, and shared experience. That gap is where Expecting Together was born.

Today, Expecting Together creates prenatal social clubs led by experienced nurses and educators, offering both practical education and a trusted space for honest conversation. Parents leave with the knowledge they need—and a built-in community and helpful group chat to lean on during those first months of family life. Expecting Together is currently active in Chicago, with a vision to expand nationally—because parenthood shouldn’t feel isolating. It should feel supported, connected, and shared.

As a special thank-you to the Big Weekend community, Expecting Together is offering an exclusive discount for subscribers. If you aren’t expecting, be sure to forward this to an expecting mom or dad you know living in Chicago!

✨ For $125 off any Expecting Together prenatal social club
Use code: CHIWEEKEND125

🔗 Learn more about Expecting Together

🔗 Find the best upcoming cohort for you

📲 Follow Expecting Together

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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