Family Vacation Spots From Milwaukee

Planning a family getaway from Milwaukee? Explore the best family vacation spots with direct flights from Milwaukee’s airport, plus discover the best Midwest Destinations like Chicago and St. Louis.

For adventurous families, read about international destinations including tropical escapes and cultural trips to Europe.

Whether you’re looking to stay in the Midwest or want to relax on a sunny beach for Spring Break, our guides offer top travel tips and activities for unforgettable family adventures.

Oct

The Gwen Chicago Review: A Walkable Mom-and-Daughter Weekend in the Loop

October 28, 2025Calie HerbstFamily Vacation Spots

When you’re planning a mom-and-daughter weekend in Chicago, location is everything. When we visit, we want to walk to all the best attractions without hailing a single cab. On our recent girls’ trip, my daughters and I stayed at The Gwen, a Luxury Collection Hotel, and it turned out to be the perfect mix of style,...

Oct

360 Chicago vs. Skydeck: Which Observation Deck Is Best for Kids?

October 23, 2025Calie HerbstDay Trips From Milwaukee, Family Vacation Spots

Lying on the glass floor of The Ledge, surrounded by sweeping views of downtown Chicago. When you’re planning a family trip to Chicago, chances are both 360 Chicago at the John Hancock Center and the Skydeck at Willis Tower pop up on your list. They both promise incredible views and unforgettable photo ops – but which one’s really worth it for...

Jul

Pueblo Bonito Los Cabos Review (2026): Best Family Resort in Cabo?

July 5, 2025Calie HerbstFamily Vacation Spots

Updated for 2026 Enjoying the pool and beachfront at Pueblo Bonito Los Cabos Resort When we started planning our family vacation to Cabo San Lucas, we knew we wanted somewhere warm, sunny, and packed with activities for all ages. After many hours of research, we decided on Pueblo Bonito Los Cabos, a Mediterranean-inspired resort with...

Jul

Best Things To Do in Kauai With Kids (2026 Guide for Families)

July 2, 2025Calie HerbstFamily Vacation Spots

Updated for 2026 Kauai is one of the best Hawaiian islands for families, especially those who love nature, slow pace, and outdoor adventures. Planning a family trip to Hawaii and wondering what to do in Kauai with kids? From beaches and boat tours to easy hikes and local treats, Kauai offers unforgettable adventures for toddlers, big...

Mar

Is Kennedy Space Center Good for Kids? Our Honest Review After Two Family Visits (2026)

March 16, 2025Calie HerbstFamily Vacation Spots

If you’re wondering “Is Kennedy Space Center good for kids?” — the short answer is yes. Absolutely yes. We’ve visited twice now with our three kids — once when they were 2, 4, and 6, and again years later when they were 9, 11, and 13 — and both times were completely worth it. It’s the kind of place that grows...

Mar

What to Take to the Beach With Kids: The Ultimate Family Beach Day Checklist

March 15, 2025Calie HerbstFamily Vacation Spots

Heading to the beach with kids is always an adventure, and being prepared makes all the difference. A beach day with kids can be the best kind of summer memory — warm sun, sandcastles, waves, snacks, and that blissful moment when everyone is finally rinsed off and tired in the good way. But it also...

Mar

10 Family Travel Ideas From Real Families Who’ve Been There (2026)

March 7, 2025Calie HerbstFamily Vacation Spots

There’s nothing quite like exploring a new place through your child’s eyes – even if the journey involves spilled snacks, forgotten swimsuits, and a few meltdowns along the way. We’ve pulled together our favorite family travel destinations, all tried and tested by families like yours. From beach resorts to international towns to weekend getaways, there’s...

Jan

Best Weekend Trips & Direct Flights From Milwaukee (2025)

January 31, 2025Calie HerbstFamily Vacation Spots

Play area for kids in Mitchell Airport. Updated August 22, 2025 Traveling with kids doesn’t have to mean long layovers or complicated connections. From MKE, you’ll find direct flights to some of the best U.S. destinations, making quick weekend trips from Milwaukee with your family easier than ever. But the good news is that you...

May

10 Best Things To Do in Rothenburg Ob Der Tauber With Kids (2026)

May 23, 2024Calie HerbstFamily Fun Hub, Family Vacation Spots

The town is compact and extremely walkable for all ages. Old World Disney Charm. Incredible History. Delicious Schneeballs. Rothenburg Ob Der Tauber was a dream come true for our family. We recently spent four unforgettable nights there with our children, ages 8, 10, and 12, as part of a tour through Bavaria. This trip will...

Sep

15 Free Family Activities in St. Louis, Missouri (2025)

September 8, 2022mkewithkidsFamily Fun Hub, Family Vacation Spots

Perhaps best known for its iconic Gateway Arch and blues music scene, St. Louis is one of the biggest cities in the Midwest. It has a rich history. This is where Lewis and Clark began their expedition in 1804, where the Supreme Court heard the pivotal Dred Scott case, and it was host to the...