seattle to dc in 2 weeks

Our family is planning a cross-country road trip from seattle to washington d.c. by way of minnesota, chicago, cleveland, hershey, and washington dc. Is this doable roundtrip in two weeks? What should we plan to see on our way there. And which routes are most scenic. We only have one time constraint, we have to be in minneapolis by the afternoon of august 15 for a martial arts tournament. Any suggestions would be greatly appreciated. Thank you in advance!

5500 miles round-trip,(by the shortest possible route) will require a good deal of "hammer-down" to accomplish in two weeks. But sure, it is doable. But the time constraints would tend to suggest that you will be using the Interstates much of the time.