Chicago’s Best Family-Friendly Events to Look Forward To

Keeping the kids entertained, stylish, and fed without losing our minds? That's the real mom magic trick. Luckily, here in the Windy City, we've got more going for us than deep-dish and dodging pigeons at Millennium Park. There are so many fabulous family-friendly events Chicago moms can actually look forward to. And guess what? You don’t have to show up in stained leggings and a coffee-stained tee… unless it’s your aesthetic.

We’ve rounded up what’s coming up, what to mark on your fridge calendar (you know the one with the broken marker cap?), and what to wear from Lola and the Boys to keep your minis looking like rockstars while they run off cotton candy energy

Because yes, moms deserve a social life too, and this one comes with snacks, sunshine, and sparkly sneakers.

Spring and Summer Events That Make Parenting Feel Like a Win

These are the ones that make us actually want to leave the house before noon. Sunscreen, check. Backup snack stash, check. Matching glitter jackets? Always.

• Spring Awakening Parade, Andersonville,

  Late March to Early April.

  This cheerful neighborhood gem is perfect for littles (and let’s be real, for us too, bunny ears and brunch anyone?). Think strollers with flair, face painting, balloon animals, and the local vendors giving out goodies.

  Outfit idea: Pair the Pastel Rainbow Sequin Dress with some white high-top sneakers. She’ll sparkle harder than the sidewalk chalk art.

  This is also a great event to kick off the Chicago family events calendar, it sets the tone for a packed season of fun and frills.

• Navy Pier Summer Fireworks + Outdoor Movie Nights

  May through Labor Day, Wednesdays & Saturdays.

  Classic? Yes. Still magical every time? Also yes. The Navy Pier fireworks are a must for those balmy summer nights when bedtime magically extends by two hours.

  Pro tip: bring a picnic blanket and grab some Garrett’s popcorn (the caramel kind gets stuck in their teeth but it’s worth it). Don’t forget your phone because the Insta pics at golden hour are unmatched.

  What to wear: The Light-Up Dino Hoodie for the boys, and for girls, the Glow in the Dark Unicorn Set. Practical and glowing like a dream? Win-win.

  By the way, this is one of the best things to do in Chicago with kids, especially when you just want them to run around and burn off bedtime resistance.

• 3. Chicago Children's Museum Free Family Days

  Select Mondays every month.

  We love a good freebie, especially one that’s educational and gives us an excuse to leave the house in cute denim and not just for Target.

  Hands-on exhibits, art projects, and enough creative stimulation to justify that post-event nap (for them… or you). It’s the kind of day where they get paint in their hair, and we pretend we’re cool with it.

  Styling tip: We’re loving the Patch Denim Jacket layered over the Happy Face Tee, makes cleaning up finger paint a little more fashionable.

  And yes, you can sneak a Starbucks on the way in.

Fall Events That Bring on the Cozy (and the Candy)

Let’s be honest: fall is a fashion mood and a memory-maker. We’re talking pumpkin patches, apple cider, costume parades, and a thousand chances for you and your kids to twin in the cutest outfits.

• Lincoln Park Zoo Fall Fest

  Every weekend in October

  Free to enter and full of festive chaos, this is hands-down one of the most fun things to do in Chicago with kids during the fall. Giant inflatables, a corn maze, pumpkin carving stations, and, bonus, real animals. Pro tip: get there early before it turns into a stroller traffic jam.

  What they’ll love: The Candy Pink Sparkle Tracksuit is cozy, glittery, and totally photo-ready for the hay bale pics. Add the Magic Beanie and your little one’s an instant autumn style icon.

  It's one of those iconic spots that always makes the Chicago family events calendar, and for good reason.

• Pumpkin Parade in Lakeview

  Late October.

  Trick-or-treating down Southport Ave with free candy at every shop, music, photo ops, and costume contests. Honestly, it’s like a mini Halloween dream, and it wraps up before bedtime. That’s what I call luxury parenting.

  Costume ideas from Lola and the Boys:

  • Rainbow Unicorn Onesie (because magical naps after trick-or-treating? Yes, please.)
  • Tiger Sequin Setfor the kid who wants to look fierce and fabulous.

  Also, let’s not pretend we don’t sneak a few mini Kit Kats out of the pumpkin bucket.

• Jack’s Pumpkin Pop-Up

  Mid-September to Halloween.

  Located in Goose Island, this one’s perfect for older kiddos and tweens who love Instagrammable moments and carnival games (you know, the ones that somehow cost $5 a play and win them a stuffed hot dog?).

  You’ll find axe throwing (for the dads, obviously), pumpkin beer (for us…kidding… maybe), and over-the-top pumpkin decor that screams “fall family photo shoot.” Bonus: There’s a corn maze.

  Dress to impress: The Metallic Bomber Jacket is a tween fave. Add Star Sneakers to complete the look.

  Honestly, events like this should be marked in bold on the Chicago family events calendar every year.

Apple Fest in Lincoln Square

First weekend of October Yes, the donuts are hot, the cider is cold, and yes, you’ll leave with a bag of honey crisps and a new candle you’ll swear was worth $18. Between the live music, kids' zone, and food booths, this is the low-key weekend win you need.

Outfit inspo: Dress the kiddos in the Cozy Colorblock Pullover and pair it with classic jeans for that effortless “I totally planned this outfit” vibe.

This is one of those things to do in Chicago with kids that’s chill, affordable, and lets you snack without guilt. (Yes, I did eat three apple fritters. No regrets.)

Winter Events That Make Freezing Worth It

Once the weather hits "I can see my breath" status, we’re still out here, layering cute coats and shoving mittens into every pocket we own. Why? Because family-friendly events Chicago offers in winter are seriously worth bundling up for.

• ZooLights at Lincoln Park Zoo

  November 22 – January 5.

  It’s sparkly. It’s magical. And it’s free most weekdays! ZooLights turns Lincoln Park Zoo into a glowing winter wonderland with music, light tunnels, and Santa photo ops (the good kind, where he doesn’t look tired yet).

  Warm & wow-worthy: The Rainbow Puffer Jacket. It’s cozy, puffy, and basically screams holiday card photo. Add a Shiny Sequin Hat and you’ve nailed festive chic.

  Hot cocoa is mandatory. So is charging your phone, because these photo ops are next level.

• Christkindlmarket Chicago – Daley Plaza

  Mid-November to Christmas Eve We go for the cinnamon sugar pretzels, stay for the tiny mugs, and leave with handmade ornaments we swear we’ll remember next year. Christkindlmarket is a yearly tradition that’s loud, crowded, and completely worth it.

  Bundle up in: The Sequin Sherpa Hoodie. It’s cozy enough for frosty nights and sparkly enough for holiday magic. Add matching boots and your girl is runway-ready, even if she’s just eating strudel.

  This one’s high on every Chicago family events calendar, and always a hit.

Pro Mom Tips for Event Days

• Keep snacks in every pocket. Every. Single. One.
• Stash mini first-aid kits in the stroller or purse, band-aids solve so many things.
• Make sure you always bring backup outfits. One for them. One for you (yup, apple cider spills are real).
• Use bribes. Bribes are fine. We call it “negotiation.”

And if you take nothing else from this, take this: bring wipes. And shop Lola and the Boys. That’s your real power combo.

Shop the Looks That Make Every Event Shine

Survive the chaos? Sure. But looking fabulous while doing it? That’s the goal. Every hayride, rink skate, and spring fest is a chance for your kiddo to show off style that’s equal parts comfy and cool.

That’s where Lola and the Boys comes in. From sparkle-filled jackets and unicorn-inspired dresses to the best boys’ joggers and glow-up accessories, everything is made with love (and moms in mind). Our pieces are durable enough for Chicago weather, and stylish enough for every memory you’ll snap.

Go ahead and build that seasonal wardrobe. Lola and the Boys has your back (and your baby’s look).