Entertaining family stopovers on a driving trip from Pittsburgh, PA, to Chicago, IL [closed]

If you have only the toddler (and not, say, a 6 year old and 12 year old as well) I don't think it matters much where you stop. A full on amusement park is wasted on someone who can get hours of joy from a cardboard box or a stick (or, luxury, a cardboard box AND a stick.) You're wise to plan a route that takes you into towns large enough to have parks with playgrounds, yet small enough that it's easy to find the park and what ever other amenities you need. Don't talk it up before you've found it, and be prepared to drive past a few if you don't like what you see in the first. A little running on the grass, a little time on the slides, swings, etc and you'll have a tired and happy toddler.

There is a reason why McDonalds have PlayPlaces. They know you're looking for that sort of thing. Probably best to decide in advance if that's something you want to use.

Know your route well - pulling off the highway mid nap because you're pretty sure this is your last chance for gas in 500 miles is not fun. If you keep food and drinks and such in the car, don't let the gas go below 1/4 tank, and use GPS or smartphones to reassure yourself that there will be another place to stop in 30 or 60 min, then you can let a nap roll on and just chew up some mileage.

I've done this drive in reverse a few times with toddlers, and the best option in my opinion: tollway service plazas ("Tollway Oasis" in Chicago lingo). On the Ohio turnpike, there are a number of them; about one every forty miles or so. Indiana has a similar set as well, though not as frequent.

These have gas, food, toilet, but more importantly have a lot of room - covered, indoors room - to run around in. If the weather is good, they also have green spaces to run in outside that in most cases are reasonably safe from cars. Bigger areas than a McDonalds or similar, and don't require a purchase (though if you're me, you'll want to). They're also great places for changing diapers, which is pretty important at that age.

Toddlers aren't going to be particularly interested in attractions (unless you stop in a zoo perhaps, but that seems like too long of a stop); what they need is running around. And as far as adult friendly, at least for me I find these plenty friendly: they have Starbucks!

They also allow something that can be fun with older toddlers: truck watching. If it's daytime, anyway, you can either sit by the side near the trucks, or sit near the bridge on those that are over a bridge and watch truckers fill up, clean their cabs, or do any number of interesting things - or just drive by, as my kids love to watch.

If you're not in a hurry, you could go down and take I70/I65. It will take a couple extra hours, but the driving is a lot better (fewer trucks, better road). And then you can stop at the Air Force Museum at Dayton.

The Rock and Roll Hall of Fame in Cleveland, Ohio, is definitely worth a visit. I think it would be relatively suitable (or at least accommodating) for a toddler.