Traveling from the Midwest with Young Kids: Tips for Smooth Adventures

Traveling with little ones can feel intimidating — especially when you’re starting from the Midwest, where distances to big destinations can be long. But as a travel agent, mom of three, and theme park enthusiast, I promise it doesn’t have to be stressful. With the right prep (and a few must-have products), you can make the journey just as memorable as the destination.

Before you pack the car or head to the airport, check out my Amazon storefront where I’ve rounded up my favorite family travel items — from travel sound machines and airplane toys to car organization must-haves. These are the exact items I use to keep my kids entertained, comfortable, and happy while we travel.

Air Travel with Young Kids

Flying with kids can feel overwhelming, but a little planning goes a long way toward making your trip smooth.

1. Choose the Right Flight Times

If possible, aim for flights that align with naps or early morning departures. Kids are often more cooperative earlier in the day, and red-eyes or late-night flights can backfire with overtired toddlers.

2. Pack Smart & Light

Bring only what you need onboard— but don’t forget the essentials: snacks, comfort items (like a favorite stuffed animal), wipes, extra clothes in the carryon (I swear it never fails that one kid will always have some sort of bathroom accident/blowout), and plenty of activities. I love having a small “surprise bag” of toys or sticker books to pull out mid-flight to keep little hands busy. Check out my storefront for our favorite travel gadgets.

3. Snacks are Your Best Friend

Airport food isn’t always kid-friendly (or budget-friendly). Pack a variety of mess-free snacks like pouches, crackers, and fruit snacks to keep little bellies happy and meltdowns at bay.

4. Be Strategic with Seating

If your budget allows, consider paying for seat selection so your family can sit together. Window seats are great for keeping kids entertained with views, while aisle seats make bathroom trips easier.

5. Prep for Security

The TSA process can be tricky with kids. Wear slip-on shoes, have your liquids bag accessible, and prep kids ahead of time about what to expect. Baby food, formula, and breast milk are allowed in reasonable quantities — just tell the TSA agent before you go through screening. My biggest suggestion: Get TSA PreCheck! Kids under 12 can go through with you, which means shorter lines at security, skip unpacking the liquids, taking off shoes, or pulling out laptops. Plus, if you have an American Express credit card, you can actually get TSA PreCheck for free — just pay with that card at your appointment and you’ll be reimbursed. This one tip alone makes flying with kids so much smoother.

6. Bring the Car Seats (If You Can!)

You can check car seats for free — but bringing them on the plane is by far the safest way to travel with little ones. Your child will be secure in a seat they’re used to, and it prevents damage that could happen if the seat is handled roughly by baggage crews. I’ve checked car seats plenty of times, but whenever possible, I prefer to bring them onboard so I know they’re safe and ready for use when we land. Plus, my children behave best when we have their seats. Car rental companies do offer car seats for an additional cost but those have always grossed me out and you don't know that they are taken care of properly.

Road Trips with Young Kids

Driving can be a great option when you’re traveling from the Midwest — but keeping kids happy for hours at a time takes planning.

1. Break Up the Trip

Plan regular stops to stretch, run around, and grab a snack. Look for parks or playgrounds along your route for quick energy burn-offs. If you're local to western WI: Be sure to check out my road trip guides that include some of my favorite places to stop along major highways and interstates — perfect for breaking up those long Midwest drives!

2. Entertainment is Key

Pack a mix of screen-free activities (coloring books, window clings, travel games) and screen-time favorites (downloaded shows and movies). A car organizer or basket can help keep everything within reach.

3. Comfort Matters

Bring cozy blankets, travel pillows, and favorite stuffed animals. A well-rested, comfy kid is a happy kid.

4. Snacks, Snacks, Snacks

Keep a small cooler with easy-to-grab options like cheese sticks, cut-up fruit, and water bottles. Bonus tip: hand out snacks one at a time to avoid messes and boredom eating.

5. Stay Organized

Use seatback organizers or bins to keep toys, wipes, and other essentials handy. No one wants to dig through a packed trunk while parked on the side of the road.

Ready to Plan Your Next Family Adventure?

Traveling with young kids doesn’t have to be overwhelming — with the right strategy (and the right gear), it can actually be fun! Whether you’re road-tripping to a nearby city or flying across the country, I’d love to help you plan a stress-free family getaway.

Fill out my planning form and let’s start building your perfect trip.