So my husband and I are taking a road trip from Boston to Mount Rushmore at the end of April. Trip will be a week. We've never been and don't want to miss quirky, fun, cool stuff along the way. Or must stop for food places, or must sees.
Any suggestions would be helpful! We have a facebook page for it, www.facebook.com/roadtripwiththehilks ha!

One week total? Fly to Denver and drive to SD.

Well, it's 60 hours of driving round trip, even if you don't stop to use the bathroom (Depends are your friends) or stop to eat (go to Trader Joe's and stock up on Clif bars and jerky). That's twelve hours a day BEHIND THE WHEEL not on the road.

So that's five twelve hour days of driving out of the seven you've got, five twelve hour days of the most boring driving in the US, I-90 . How boring? Remember the scene in "North by Northwest" where Cary Grant gets off the bus and is cased by a crop duster? That boring.

Add to this the fact that I-90, particularly in Ohio is famous for speed enforcement, and it will not only be a long boring trip but a long SLOW boring trip.

You could spend one of your two days of leisure seeing Mt Rushmore and the Black Hills and the other in Chicago, morning at the Art Institute, afternoon in Oak Park seeing Frank Lloyd Wright houses.

Or you could fly to Rapid City with a layover in Chicago on the way out.

Fly to Rapid City and rent the car there. And/or do the Chicago layover. With more time in the BH you could also include Devils Tower, the infamous Wall Drug, ALL of those caves, casinos, the jackalopes, etc., etc.

I agree with flying to Rapid City and renting a car. You will spend all your time driving and it is boring. We've done it. Consider flying and staying at Custer Park and have some fun/relaxation: http://www.custerresorts.com/