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Trips We’ve Loved / Weekend Ideas

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Easy Weekend Getaways (2–3 nights)

 
Vanessa Kent profile picture
One of our favorite easy weekend trips. It’s close enough to feel doable but different enough to feel like a true getaway. Between great food, walkable neighborhoods, museums, and kid-friendly attractions, Chicago works just as well for a family trip...
City of Chicago
 
Vanessa Kent profile picture
An easy, kid-approved weekend getaway. With waterparks, family-friendly hotels, and lots to do in one place, the Wisconsin Dells is perfect when you want a fun trip without a lot of planning. It’s especially great for a 2–3 night stay and works well ...
Wisconsin Dells
 
Vanessa Kent profile picture
A great option when you want something relaxing but still close to home. Lake views, walkable areas, boat tours, and plenty of spots to eat make Lake Geneva perfect for a low-key weekend. It works well for both a couples’ getaway or a slower-paced fa...
Visit Lake Geneva

Family Trips That Worked

 
Vanessa Kent profile picture
One of our favorite truly stress-free trips. This resort is family-friendly without feeling chaotic—great food, beautiful grounds, and everything you need in one place. It’s perfect if you want a relaxing vacation where the kids are entertained and y...
Hotels in Riviera Maya
 
Vanessa Kent profile picture
Busy, magical, and absolutely worth it. There’s nothing quite like seeing this park through your kids’ eyes—classic rides, parades, and that Disney magic that makes the long days feel memorable. It takes planning, but it’s one of those trips that bec...
Magic Kingdom Park