Brad, if you do come down the Wisconsin side, and if you do indeed get to La Crosse, here are a few suggestions you might like:
In the small town of Fountain City is the Golden Frog, a restaurant and bar that has been around for many decades. I grew up in the area, and remember going to that place in the late 1950's with my folks. Very good food, and it's really more like a supper club, except they are open for lunch too.
Motorcyclists in the Twin Cities area have a yearly thing they call the Flood Run, where hundreds of bikers, of all kinds, real outlaws and regular riders, ride up and down the river from Twin Cities to Winona and back. The Golden Frog is a regular stop, and is a real hoot when all those rowdies are there. But no one is looking for trouble, they are all out for fun. www.thegoldenfrog.com
Immediately across the street (Hwy 35) from the Frog is a lefse place, homemade right there. Can't get it any fresher. Don't remember the name. But really nice people...well, of course they are. They're Norwegian.
Ten miles south on Hwy 35 is the Hillside Fish House, a very good supper club (not open until 5 PM), but they have been there for well over a century, and the menu explains trading with the Indians for fresh fish. This place I remember with my folks since the early 50's, always been good, and looks just like it always did. But it would be an hour stop for your family if you were to eat there. www.hillsidefishhouse.com
You will probably be going through Trempealeau on your way south. If you feel like making a stop, there is the Hungry Point, a combination boat dock, bait shop, and bar and grill. I have not been there for a couple years now, but they had great burgers and fries and onion rings, and it is a true Roadfood place, filled with local color and characters. Great view of the Mississippi and the local lock and dam from their bar area.
But it sounds like you are interested in making time to get home. Instead of chicken pot pie to take home for dinner that night, how about barbeque? We have a very good place in La Crosse, Train Station Barbecue. It's very well done by an accomplished chef, and leaves Famous Dave's way back in the dust.
The name is probably too much to explain right now, but they are a drive-thru place and very fast. And reasonably priced.
They serve their meat dry, with sauce on the side, the perfect way. They have great sauce, but the food is so good you don't need much. I've always liked Bone Sucking Sauce for it's thinner, vinegary flavor and texture. This place goes in that direction, but in a much better way. When I have their sauce, Bone Sucking suddenly seems too sweet.
Besides the sauce, their beans are incredible. Get a pint for sure. The corn bread is also good, but the cole slaw is kind of large chunks and flavorless, and the potato salad is pretty good, but no eggs in it, which I like. I will usually add some at home.
But they are made for takeout, and everything they do travels well. I do love their rack of ribs, and pulled pork. www.thetrainstationbbq.com
But La Crosse also has the famous chains Maidrite and Happy Joe's pizza. The Maidrite store in La Crosse is a great throwback to older times, not at all the plastic kind of places they are now producing. Talking Roadfood style, you'd love it. Old style local building, local neighborhood, local people, no one else even seems to know about it. But they have all the Maidrite menu, and more. Great breakfasts, and steaks too!
Happy Joe's is the home of their well known taco pizza, and mighty good. Where Train Station and Maidrite will require you to go into town a little, Happy Joes is right close to I-90, and you will see it (on your left) in the suburb of Onalaska if you are coming down Hwy 35. Then it's just a half mile or so to I-90.
Depends on what your family feels like eating, and your schedule, but I would really recommend Train Station Barbecue. I can't go near there without getting a half-rack and some cornbread. My wife is a big fan of their pulled pork.
Good luck! I hope these links work, if not they are all just a google away.