Duquesne, that is.

Pittsburgh is a great place to stop. The Carnegie museums are great fun, especially the Science Center and Sportsworks. Don't know that the baby would get much out of them, but the 3-year-old definitely would. The zoo and the Dusquene Incline would also be fun.

Right above Pittsburgh, there is a hotel with a small water park. You will see a million signs for it so you can't miss it. The Cleveland area is great for kids. You could consider Kalahari Water Park.

We used to make that car trip every year growing up so we could bring our dog to our grandparents house (grew up in lived in DC, grandparents in Chicago). There are a lot of mega rest stops in Ohio, and a lot of very family friendly Holliday Inns, if you just don't want to drive all day and break up the trip so it's easier with kids. We always did that--nothing special on the way there, but found a large Holliday Inn with a nice pool just to keep everyone from going nuts.

Off the top of my head, I can't think of anywhere along PA, OH, IN route that's along your destination. It's been years since I drove to where you're going, I'm originally from Milwaukee and went to school at Madison. (Go Badgers!) I wouldn't even think of driving there w/ small kids unless I had a bunch of time on my hand where I could break up the trip but even still, a lot of time on the road for a small child to take, but that's just me. My 4 yr old would go nuts being in the car for so long. I can hear him saying "our we here yet?"

I'm considering taking a road trip this summer with a 3 year old and almost 1 year old where the first place that I would want to stop would either be Chicago, IL or Madison, WI (friends/family in both places). The 11 hour drive to Chicago was totally doable pre-kids but I think that now, without DH (he will meet up with us later), it might be miserable. Is there anywhere interesting that we could stop on the way? Or at least somewhere that's not very out of the way to break the trip up? I'm not opposed to car camping. Is this the worst idea ever?