Spring Break in Chicago

Last week, I took a break from the blog to spend a week in Chicago with my family for spring break. We packed a lot into just three days before wrapping up the trip with my in-laws, who live just outside the city. The kids were absolute troopers, handling the long walks, packed itinerary, and lack of quiet time like champs.

If you're planning a trip to Chicago (or any big city!) with your kids, I’ve put together a list of our favorite places, along with road trip and hotel tips to make your travels smoother.

Road Trip Fun: The Journey Begins

Before reaching Chicago, we made an exciting pit stop at Warm Springs Ranch in Booneville, MO—the home of the Budweiser Clydesdales! The kids were thrilled to pet the horses, take pictures, and tour the facility. It was a perfect surprise and a great way to break up the long drive.

📝 Road Trip Tips for Traveling with Kids

✔ Pack Easy Meals: Peanut butter sandwiches or simple snacks help avoid the endless cycle of drive-thru stops.
✔ Special Snack Box: I packed a lunch box with snacks they don’t usually get. My kids loved the YUM EARTH and UnReal brands—a healthier alternative without artificial dyes.
✔ Keep Kids Entertained: The Target dollar spot had road trip BINGO boards, and Ollie’s had fantastic discounted activity books and crafts for the ride.

🏨 Hotel Hacks for a Smooth Stay

A new environment can be exciting but also overwhelming for kids, so I made sure to bring a few comforts from home.

📝 Tips for Hotel Stays with Kids

✔ Pack Favorite Comforts: Each kid brought a small blanket and stuffed animal (easy to wash when we got home).
✔ Bring a Sound Machine & Story Player: We always travel with our Toniebox, and each child picked a story to share.
✔ Use Hotel Rewards & Free Breakfast: We used rewards points for our stay, and free breakfast helped us save time and money.
✔ Activity Tote for Downtime: I packed coloring books, markers, travel-friendly games, LEGO for my son, and bracelet-making kits for my daughter—perfect for winding down.

Our Chicago Adventures

Day 1: Dinosaurs, Navy Pier & Sky-High Views

📍 Field Museum – Seeing SUE the T-Rex was a must! (If you want some backstory, watch the "Dinosaur 13" documentary on Amazon Prime—crazy story about how the Field Museum acquired her fossils!)
📍 Navy Pier – Ferris wheel rides, a 3D maze, teacup rides, and classic pier snacks made for a fun-filled afternoon.
📍 John Hancock Building – I am not a fan of heights, but the kids loved seeing the breathtaking city views.

Day 2: Underwater Wonders & Over-the-Top Treats

📍 Shedd Aquarium – The beluga whales and penguins were the favorites!
📍 Miracle Mile Stroll & American Girl Store – A must for any American Girl doll fans.
📍 JoJo’s Shake Bar – Their insanely over-the-top milkshakes were more of an experience than a treat (we couldn't finish them!).

Day 3: LEGO Land & Medieval Times

📍 LEGOLAND & Peppa Pig World (Schaumburg, IL) – About 40 minutes outside the city, this was pure magic for the kids! The Peppa Pig Adventure was actually located in a mall. Blast from the Past: Visiting an Actual Mall – Walking through the mall in Schaumburg, smelling Mrs. Fields cookies and Auntie Anne’s pretzels, seeing stores bustling with people—it brought back so much nostalgia. It made me realize how much has changed in just a short time. Indoor malls were such a huge part of my childhood, yet this was the first time my kids had ever experienced one! It was one of those moments that made me stop and appreciate how fast things change—and how fun it is to relive pieces of the past with my own kids.
📍 Medieval Times – Picture professional wrestling, but with knights on horseback. My husband went as a kid, my niece and nephew had gone, and now it was our kids' turn to cheer on their knight.

Final Thoughts: Making Memories Over Perfection

This trip reminded me that family travel doesn’t have to be perfect to be memorable. We had our share of meltdowns, tired legs, and sugar crashes, but we also laughed, explored, and made amazing memories together.

If you’re planning a trip to Chicago and have questions about hotels, attractions, or logistics, feel free to email me!

👉 Do you have any family travel tips? Drop them in the comments!

📢 Reminder: I'll be taking a blog break from May-August to enjoy summer with my family as we settle into our new home. Thank you for reading, and as always…happy reading! ✨

Katie Marie