Raleigh to Chicago Roundtrip
Would love ideas for a 14 day roundtrip itinerary. Traveling with a teenager, so definitely thinking of stopping at Cedar Point Theme Park in OH. We like National Parks and have never been to Chicago, so want to spend about 4-5 days there and see a few things along the way. We'll be traveling in a self-contained camper van and can stay anywhere. Thank you.
...and Now for Something Completely Different
One other route between Raleigh and Chicago that I would consider (Your mileage may vary) would be one that did a wide sweep west and south of the one previously outlined. Although it looks a lot longer on a map, it's only about 200 miles more than the other one. I'll describe this one northwest bound as well, but of course you can do either route in either direction.
Again, get to Winston-Salem but for this route continue westbound using I-40 to Lake Junaluska NC and there switch over to US-19 south, If it interests you or your teenager you can stop at The Wheels Through Time Museum in Maggie Valley. Then it would be on to US-441 through Great Smoky Mountains National Park and then Pigeon Forge TN. Using TN-66 north from Sevierville would get you back on I-40 through Knoxville.
Leave I-40 at Monterey and head cross country on TN-84/52/51, then KY-163/839/90 to Cave City and Mammoth Cave National Park. If you leave the Visitor's Center on Maple Springs Ranger Station Road, you'll get a free enjoyable little trip on the Green River Ferry. You'd then do some serious back (but still two-lane paved) roading on KY-1352/1827/728/259/238/185 to the Western Kentucky Parkway. Be sure to look at all this on a map; it's easier than it sounds.
The Parkway and I-24 will get you to Grand Rivers KY and the Land Between the Lakes. It's then a relatively simple final leg to Chicago via I-24/57. Along that stretch you'll find the Lincoln Log Cabin State Historic Site for a little more surreptitious education.
AZBuck