Chicago is an amazing city full of free activities. Our beautiful parks, public lakefront, and countless free museum days - but sometimes it’s nice to splurge and break out of the library, playground, pool, rise and repeat routine. One of my favorite things about living in a world-class city is treating the summer as an excuse to be tourists and splurge on things you would normally only do on vacation.

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

So if your kid asks if they serve Piña Coladas at the community pool and has more stamps on their passport than you did by the age of 30, then this list is for you.

Planes, Trains, and Boats!

Ride in Style on an Electric Boat

Rent a family-friendly luxury Duffy boat or pastel-appointed retro boat (pictured above) and cruise the Chicago River like bougie pirates (costumes encouraged). If navigating the river traffic is too much, you can rent a donut boat or retro cruiser to cruise the North Branch part of the river for calmer “seas”.

🇬🇧 🫖 Have A Euro Adventure Day (Chicago style)

Hop aboard a big red double-decker bus for a hop-on and off city tour (my pick would be the sunset tour), then head to The Langham for their Botanic Garden-inspired seasonal tea for a proper Euro-style afternoon. If you’re feeling extra bougie, you can also book a private tour if you don’t want to rub elbows with actual tourists. 🤪

🚉 🎶 Take the Metra to a kid-friendly Ravinia concert

I'll never forget my first time at Ravinia—seeing wax dripping from a full candelabra, fresh-cut flowers, and a sterling silver ice bucket chilling a bottle of Veuve in the grass, and I knew this was my style of “picnic”. "Teach 'em young" is a phrase for a reason, and what better way to experience Ravinia than with a Metra ride (Chicago's bougiest public transport) to a kid-friendly concert. Pack a kid-approved charcuterie board from Boards by BW and a gummy tackle box from Susie’s Sugar Buzz -both local and mom-owned, delicious snack businesses - and be the envy of the lawn.

🎡 Reserve a VIP Gondola at Navy Pier

Reserve a private VIP gondola on Navy Pier’s iconic wheel—featuring plush seats, the trademark glass bottom, and glittering skyline views for you family of four. Grab lunch or early dinner @ Offshore Rooftop, the world’s largest rooftop restaurant and if you have the time, check out the much-hyped Butterfly House.

👨‍🚒 🎆 Get front-row fireworks views on a historical Chicago fireboat

Skip the touristy boats and climb aboard a vintage 1937 fireboat for a family-friendly cruise—kids love the water cannons, skyline views, and cool firefighter stories. They also offer evening fireworks cruises and still have spots open for the Air and Water Show - (hurry, those sell out fast.)

Treat Yo Selves

⛱️ 🌊 Book a Weekday Private Cabana on Lake Michigan

For those of us not having an Amalfi summer (cue the FOMO), level up your beach day with a private cabana at Oasis Shore Club and enjoy a day at the beach with Mediterranean-inspired hummus plates that will put your snacklebox to shame. Evenings and weekends are 21+, so plan your visit for a weekday.

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

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!)

🫒 Score an Outdoor Table at Aba

A perk to eating dinner before 5 PM? An open table at one of the city’s best rooftop restaurants. Yes, it’s trendy. Yes, they allow kids. Go early, order dips and fries, and watch your child vibe to Mediterranean beats and city views. (And yes, they serve butter noodles) Tack on a round of bowling next door at PunchBowl Social (all ages permitted before 10 PM) to make a day out of it.

⛺🛎️ Check In to “Camp Peninsula”

The Peninsula Chicago offers a five-star staycation experience that will delight your kids and trigger your summer camp nostalgia, complete with in-room tents, mini robes, and slippers. The package also includes kid-friendly programming like terrace games, postcard coloring, pool activities, and complimentary breakfast (is there anything better than waffles via room service?) It’s giving luxury glamping…with zero TSA lines.

💅🏾✨Treat your doll to a glowup day at American Girl

If you have a beauty and makeup-obsessed kiddo ready for her own YouTube channel - you will want to bookmark this. Let your mini stylist take over at this glam session at the AG Dolled Up Salon, where they'll give their American Girl bestie a full hair and nail makeover, and go home with a goody bag and adorable doll-sized nail polish.

Cultured Cuties

🎥 🖼️ Have a “Save Ferris” Saturday

Watching Ferris Bueller's Day Off is a parenting rite of passage - so pop the popcorn and stream it on Friday night, then on Saturday, head downtown for a Ferris-themed private tour at the Art Institute. While sadly Chez Quis is as fictional as Abe Froman, La Serre in the West Loop has a kid's menu, or you can head to the French Market for Nutella crepes at Bon Appetit Creperie—both worthy substitutes that would surely impress the Sausage King of Chicago himself.

📽️🍿 Catch a classic summer movie on a Rooftop (with headphones!)

Enjoy outdoor movies with skyline views at Rooftop Cinema Club in Fulton Market. Family screenings (with both AM and PM showtimes) feature kid-sized comfy chairs, gourmet snacks, and wireless headphones (perfect for chatty young viewers). Come early for lawn games, then settle in for favorites like The Sandlot or Aladdin.

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

Beat the crowds (and the summer camp group chaos) 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.

💎⚾🌭Diamonds and Jewels: Take me out to the Rooftops

The all-inclusive rooftops at Wrigley are perfect for families. You'll find allergen-friendly food, no bathroom lines(!), a buffet of ballpark treats, and self-serve ice cream (need I say more?). Kids can move around inside during slow innings - I’m packing these Cubs jewelry kits from Supersmalls - and there's indoor viewing with AC if it’s a scorcher. While you’re not inside the Friendly Confines, it's great for those seeking the Wrigley experience with kid-friendly amenities.

🐧🦦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 tuexedo-donning crew in town.

📮 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

This post may contain affiliate links, which means I may earn a small commission if you make a purchase. Thanks for supporting!