We have stayed at the Kalahari Resort in the Wisconsin Dells for years, and it is easily one of our favorite family vacation destinations. It’s an easy drive from Chicago, and once you get to the resort, you really do not need to leave again for a fun and relaxing vacation centered around playing and eating. Arcades, an adjacent movie theatre, attractions like rides, ropes courses, bowling and go-karting, and of course, pools and plenty of fun water attractions make it super easy to enjoy lots of varied family fun without having to drive around much (or at all). When our kids were younger and not super interested in sight seeing, this was by far the most relaxing and enjoyable of all our family trips.