How to Spend a Perfect Weekend with Kids in Chicago

You know those weekends when the kids wake up early, the sun is shining, and you just know they’re not going to be content with staying home in pajamas watching cartoons? Yep, we’ve been there too. So we’ve pulled together our tried-and-true tips for how to spend a perfect weekend with kids in Chicago, with plenty of outfit inspo, fun ideas, and mom hacks sprinkled in.

A Playful + Fashionable Weekend with Kids in Chicago

If you're mapping out the ultimate weekend with kids in Chicago, we’ve got your back. Think of this as your go-to mix of all-day play, stylish snacks, photo-ready fits, and low-stress family fun. Here’s how to make every moment count, with style, smiles, and zero meltdowns.

1. Start at Maggie Daley Park

Kick off the weekend with kids in Chicago at Maggie Daley Park, aka Chicago’s most joyful energy-draining, parent-sipping-coffee-while-kids-climb paradise. There are giant slides, rock walls, rope bridges, and soft ground (bless).

Swing by Wildberry Pancakes & Cafe across the street for chocolate chip pancakes and a side of espresso therapy.

Style Spotlight from Lola and the Boys:

• Sequin Stripe Set – part sparkle, part sporty, all-day cute
• Rainbow Magic Sequin Dress – twirl-worthy with just enough whimsy to turn the playground into a runway

2. Make a Magical Stop at Lola and the Boys Unicorn World

You know that one place your kids would live in if they could? This is it. Our Unicorn World stores are packed with glitter, good vibes, and everything they’ve ever wanted to try on. Come for the sparkles, stay for the giggles and impromptu fashion shows.

• Water Tower Mall – 2nd Level
• 919 N Larrabee
• Northbridge/Nordstrom

Let them try on their new favorites, snap a few selfies, and maybe even grab something special to wear to dinner (because you know they’ll ask).

3. Midday at Navy Pier

Next up: Navy Pier. It’s equal parts classic and chaotic, in the best way. Ride the Centennial Wheel, let them loose in the Chicago Children’s Museum, and snag a bag of Garrett’s popcorn (Chicago mix, obviously).

Cute Meets Comfy:

• Pink Unicorn Bomber– the jacket that turns heads and keeps the chill out
• Chicago Hoodie– soft, stylish, and park-ready for boys and girls

Mom tip? Always carry wipes, and get your own popcorn bag. Trust.

4. Picnic at Lincoln Park Zoo

One of our favorite free gems in the city, Lincoln Park Zoo, makes every weekend with kids in Chicago feel like a little urban safari. We usually pack a picnic lunch and find a shady spot near the lions.

Don’t Forget to Pack:

• Snacks (and backup snacks)
• Picnic blanket
• Wipes, SPF, and bug spray (because summer)

Zoo-Approved Style Picks:

• Neon Sequin Tiger Sweatshirt – bold, fun, and makes them feel like the ruler of the jungle
• Sequin Bear Bomber– easy to pair with anything and guaranteed to get compliments

5. Pizza Night at Pizzeria Portofino

Wind down the day with pizza and river views at Pizzeria Portofino. It’s casual, kid-friendly, and just chic enough to justify a cute outfit change. We don’t make the rules; Chicago sunsets require sequins.

Table-Worthy Outfits:

• Hearts Sequin Dress – just enough glam without sacrificing comfort
• Glitter Star Bomber – for layering sparkle when the breeze hits

We usually order a Margherita for the table and end with soft serve. If you’re lucky, you might get through dinner without someone trying to trade you for a breadstick.

6. Slow Sunday Start: Pajamas + Pancakes

We’re all for a slow Sunday start, mismatched socks, fluffy waffles, and extra syrup included. And if we’re staying in a little longer, the kids are doing it in style.

Our Pajama Picks:

• Evil Eye Silky Set– breakfast-approved and naptime-friendly
• Happy Face Lounge Set – bright, comfy, and perfect for lazy cartoon marathons

Let them eat in PJs, then do a quick outfit change before heading out. No stress, just cuteness.

7. Sprinkle-Sweet Midday: Museum of Ice Cream

By mid-morning, it’s time to up the fun factor. The Museum of Ice Cream is basically your kid’s candy-coated dreamland, giant popsicles, sprinkle pools, pink everything, and enough photo ops to keep your camera roll busy for weeks. It's a must during your weekend with kids in Chicago, and yes, adults get ice cream too (you're welcome).

Style Picks for Sprinkle-Ready Fun:

• Rainbow Sequin Skirt – made for twirling and posing on every floor
• Unicorn Dress – pastel perfection that makes them feel like the queen of ice cream

Your camera is going to get a workout; don’t forget a power bank. Or two.

8. Beachy Lunch at North Avenue Beach & Castaways

Once the sugar rush starts to level out, head to North Avenue Beach for sand, sunshine, and lakefront breeze. Castaways is right on the beach and has a chill, summery vibe. Order lunch while the kids dig sand holes or throw themselves dramatically into shallow water (it’s their thing).

What You’ll Need:

• Sand toys
• Sunglasses + hats
• Change of clothes (because wet sand is inevitable)
• Sunscreen, you will regret skipping this

We like to let them play while we sip something cold with a side of fries. Parenting win.

Mom Hacks to Keep Things Running Smoothly

Every mom knows that behind every picture-perfect weekend is a bag full of snacks, backup outfits, and about five unplanned detours. These quick hacks will help keep your weekend with kids in Chicago smooth, stylish, and meltdown-free.

1. Keep It in the Bag: - We keep a weekend-ready backpack by the door, stocked with:

• Wipes
• Refillable water bottles
• Mini first-aid kit
• Reusable snack bags
• Foldable blanket
• A backup hoodie (because Chicago weather is a surprise every 20 minutes)
• Swimsuits
• Towels
• More snacks (always more snacks)
• Flip-flops or backup shoes

2. Prep Outfits the Night Before

Trust us on this one, lay out the outfits. Kids feel special when they get to help choose what to wear, and mornings move faster when we’re not trying to track down that one glittery sneaker.

3. Screenshot Addresses & Parking Info

Between playgrounds, piers, and ice cream museums, hopping around the city can get chaotic. Screenshot locations and parking tips ahead of time so you're not frantically Googling with a hungry toddler on your hip.

4. Keep a Stash of Quarters and Dollar Bills

For those splash pad lockers, random carousel rides, or bubble machine vendors that only take cash. You’ll feel like a superhero when you actually have it on hand.

Every smooth weekend doesn’t come from a flawless plan, it comes from being just prepared enough to enjoy the chaos. With a few smart mom hacks (and plenty of snacks), you’ll be ready for anything Chicago throws your way, sparkles, spills, and all.

Why Lola and the Boys Is a Must for Stylish Moms

So now that you’ve got a full itinerary for the ultimate weekend with kids in Chicago, let’s talk logistics. Because yes, these are all fun, fabulous plans, but we’re also moms. We know snacks will spill, moods will shift, and someone will definitely lose a sock. Here’s how we stay stylish, sane, and totally ready for anything from tantrums to tourist traps.

We design everything at Lola and the Boys with your kiddo in mind, and your schedule. That means magical pieces that move with them, glitter that doesn’t itch, and quality that survives the sixth spin through the washing machine. Whether it’s weekend play or a birthday bash, we’re here to help your mini shine.

Shop Lola and the Boys now to grab all the standout looks featured in this post, before they disappear faster than a churro at Navy Pier.