Chicago is full of wonderful free experiences — parks, museums, lakefront walks, neighborhood gems. But if you’re staying in the 3rd Coast this spring break, it’s a good excuse to elevate the ordinary.

One of my favorite things about living in a world-class city is treating a week off school like a thoughtful staycation — exploring Chicago in a way that feels intentional, memorable, and just a little elevated. Whether you’re spending Spring Break in the city or simply looking for new ideas to mix up your usual routine this Spring, there’s something here for everyone — from the sports fanatic to the emerging artist to the mini foodie in training.

Inspired by Town & Country's A Snob's Guide, this is my carefully curated list of Chicago activities for discerning parents and our slightly high-maintenance kiddos.

Where to Stay

The most-kid friendly luxury hotels in Chicago

🧸 The Langham x Chicago Children’s Museum Kids Suite

The Langham (one of the most beautiful Chicago hotels IMO) partnered with Chicago Children’s Museum to create an exclusive Kids Suite for hotel guests — complete with skyline peg walls, interactive game features, a ball play nook, soft terrain for littles, and museum-inspired educational toys. It’s a private play space within a five-star hotel and an easy built-in activity between outings.

🎬 InterContinental “Dive-In” Movies & Mermaid for a Day

Dive-In Movie Nights take place every Friday and Saturday from 6:00–8:00 PM at the InterContinental on Michigan Avenue (for hotel guests) featuring family-friendly films, snacks, refreshments, and oversized floats — all inside one of Chicago’s most iconic pools.

For a special Spring Break event, Mermaid for a Day returns Sunday, March 29 from 1:00–3:00 PM. Designed for children ages 5 and up, kids can swim with mermaids, enjoy story time, snack on treats, and head home with a themed goodie bag. You don’t need to be a hotel guest for this experience and can book via ResortPass (make sure you select March 29.)

🍿🍦 Four Seasons Chicago: 5-Star Movie and Ice Cream Night

Just blocks from Lake Michigan, Four Seasons Chicago pairs luxury with genuinely thoughtful family amenities. Young guests are welcomed with the Sammy the Skyscraper activity book and can participate in an interactive Adventure Passport scavenger hunt throughout the hotel.

Families also have access to the Kids’ Room on Floor 32, featuring arcade games, crafts, and books, plus themed family movie nights (including Trolls on March 20 and Zootopia on March 27; $20 adults / $15 kids for hotel guests only).

The Roman-inspired indoor pool is open year-round, but the true highlight may be the darling in-room ice cream cart — a chance to build a towering sundae in a hotel robe, which is arguably every child’s dream scenario!

⛺🛎️ Check In to “Camp Peninsula”

The Peninsula Chicago’s seasonal “Camp Peninsula” experience brings a thoughtful summer-camp theme to a five-star stay. Rooms are outfitted with in-room tents, mini robes, and slippers, while kid-friendly programming includes terrace games, postcard coloring, pool activities, and complimentary breakfast. It’s a creative way to blend classic camp nostalgia with the comfort of a luxury hotel — no travel logistics required.

🏨🎳 Spread out in a Swissôtel Family Suite

Swissôtel Chicago offers family-friendly suites with a separate but adjoining themed room just for kids — complete with playful décor, a kid-sized table and chairs, coloring books, games, and an in-room teepee for cozy downtime. It’s a thoughtful setup that gives children their own space while keeping everyone close.

Mom and dad can have their own room and separate bath and shower and access to the Penthouse Fitness Centre — all within walking distance of Millennium Park and Michigan Avenue.

What to Do

So No One Says “I’m Bored!” (At Least This Week)

💗 💚 A Wickedly Fun Chicago Day

Grab your emerald sparkle from Lola and The Boys and plan a Wicked-themed city day. Start with Defying Gravi-Tea: For Good at The Langham — an immersive, Oz-inspired afternoon weekend tea running through March 29. Then head to the Griffin Museum of Science and Industry to experience the Paul Tazewell exhibition, showcasing the artistry behind iconic costumes from Wicked, Hamilton, and more — including Glinda’s pink bubble dress and Elphaba’s Emerald City gown.

⚾🌭 Behind-the-Scenes at Wrigley Field + Dinner Nearby

Make your Cubs fan’s day with a behind-the-scenes tour of Wrigley Field, where you can explore the dugout, press box, and ivy-lined field while learning about the ballpark’s storied history. Afterward, walk to nearby Swift & Sons Tavern for an early dinner. From 4:30–6:30 PM, kids eat free with the purchase of an adult entrée — an easy, family-friendly way to wrap up your Wrigley day.

🧖‍♀️ Relax with a 5-Star Pool and Spa Daycation

For ages 12+, treat your tween or teen to a luxury pool and spa day at the Four Seasons via ResortPass. Order a mini fruit plate, lounge in robes, and get mom-and-me matching mani-pedis. (Here’s $20 off a ResortPass booking for being a subscriber!)

🛍️🎀 American Girl Place Chicago – Spring Break Events

If Water Tower is already on your itinerary, check the American Girl event calendar before you go. During CPS Spring Break, they’re hosting special ticketed experiences including Spring Teatime (March 27–29), a Spring Flower Crown Party & Lunch (March 27), and Pet Adoption Day (March 28 and April 11), where girls can “adopt” a new pet for their doll. Each event includes a hands-on activity paired with a café experience, making it more than just a shopping stop.

🦖 Rise and Shine with Sue (and no crowds!)

If you have kids that are early risers—this is the moment you have been waiting for. Beat the crowds with an early-access VIP tour at the Field Museum. Arrive before opening, check out Sue the T. rex and the Griffin Halls in peace, and enjoy a guide-led, crowd-free hour before the museum officially opens to the public.

🎭✨ A Broadway-Inspired Chicago Day

If you have a theater-obsessed kiddo make spring break feel like opening night. Take a behind-the-scenes tour of The Chicago Theatre to explore its iconic marquee and grand lobby while learning about its storied past, then head to nearby Petterino's for a classic pre-theatre dinner with old-school Broadway energy. Cap the evening with tickets to Hamilton through Broadway In Chicago for a full-scale theatre experience that turns an ordinary night off into something unforgettable.

🐧🦦 Zookeeper for a Day

Skip the standard loop around the enclosures and secure your title as Coolest Parent Ever by booking a behind-the-scenes animal encounter instead. At the Shedd, you can mingle with all the VIP sea creatures - snack with the sharks, train with a beluga, and even get up close and personal with a sea otter! Prefer feathers over fins? Suit up for a Private Penguin Encounter at Lincoln Park or Brookfield Zoo, where you’ll step inside the cove and hang out with the chicest tuxedo crew in town.

Eats and Treats

Permission to add sprinkles to everything this week

🍭 Muah Character Cotton Candy (Water Tower)

Okay, yes — I’m about to suggest $30 character cotton candy. But this is the Boogie Guide, after all. If you’re already at Water Tower “investing” in American Girl and the LEGO store, you might as well finish strong at Muah Cotton Candy with a Labubu (or other character) sweet treat that doubles as dessert and an Instagram moment.

🍦🍒 Royal George Sundae @ Margie's Candies (Bucktown/Ravenswood)

If spring break calls for something over-the-top, this is it. The Royal George sundae at Margie’s Candies arrives in a silver bowl piled high with scoops of ice cream, hot fudge, caramel, whipped cream, and cherries — seriously Google it. A beloved Chicago institution for decades, it’s equal parts nostalgic and theatrical, and the perfect sweet finale to a day in the city.

🍣 Kid-Friendly Sushi @ Itoko (Lakeview)

Itoko is a relaxed but polished Japanese spot that makes sushi feel approachable for families if you’re trying to expand your picky kids palate! The kids’ menu includes a beginner sushi set and other simple, well-executed options that gently introduce new flavors while you can enjoy delicious sushi. If you don’t make it for dinner, visit for weekend brunch between 9:30–10:30 a.m., when kids 12 and under eat free.

🍩 Underground Donut Tour (Downtown)

Book the Original Downtown Tour for a guided, small-group donut crawl through River North and the Loop. The experience includes curated stops at some of Chicago’s most beloved donut shops — including classics like Doughnut Vault — while sharing stories about the neighborhood’s history and evolution. It’s interactive, walkable, and a sweet way to explore the city during spring break.

🍕 Make Your Own Pizza @ Summer House Santa Monica (Lincoln Park)

Summer House Santa Monica offers DIY pizza making Mon–Thurs from 4–6 PM, which turns dinner into a fun activity. Kids wash up, stretch their own dough, choose sauce and toppings, and watch their creations head into the oven before being delivered back to the table. It feels like a mini cooking class — plus dinner — all in a bright, beachy setting that works just as well for parents as it does for little chefs.

🍨 Sunday Monday @ Little Goat Diner (Southport)

Little Goat Diner is a family-friendly Southport staple that makes weeknight dining feel a little extra special. On Mondays, receive a complimentary mini sundae with the purchase of an entrée — an easy way to sweeten the start of the week. Can’t make it on Monday? Kids eat free on Tuesdays starting at 4 p.m. with an adult entrée purchase, making it a no-brainer for a spring break dinner out.

📮 But wait, there’s more!

Follow me on Instagram for more curated recs, hidden gems, and fun ways to make the most of family time in the city. If you try something from the guide, be sure to tag me—I’d love to see what your crew is up to! And if you know a friend who’d love this kind of content, feel free to forward this email or send them the link to subscribe.

Cheers! 
- Kaitlyn @ Big Weekend

Images: personal photography and licensed stock imagery. Exhibition image courtesy of the Griffin Museum of Science and Industry.

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