Welcome aboard the RoadTrip America Forums!

The good part about your propose journey is that the basic loop, Chicago-Yellowstone-Grand Canyon-Chicago, can be driven in seven days leaving you time for visits to the places you've mentioned. The bad part is that there's so much to see that even seven days worth of 'free time' is not enough to do an in-depth visit to any of them. If you'll be happy with a 'sampler' trip that will be as much about the drive as the places you drive to, then this should work very well for you.

What you can look at as you plan your RoadTrip is a mix of driving and sight-seeing each day. Some days will be mostly about driving, with only a few short stops. Other days will be major stops such as Yellowstone and the Grand Canyon. Unfortunately, while a day at either will be a glorious day, you could easily spend even more. On the routes between your major destinations there are other great places that you can spend a half day or so at, depending on your interests and time available. These include Badlands National Park, Mount Rushmore, Devils Tower, Little Bighorn Battlefield, the Grand Tetons, the Great Salt Lake, Bryce Canyon, Cedar Breaks, Zion, Monument Valley, Arches National Park, Rocky Mountain National Park, and the landmarks of the old Oregon Trail.

AZBuck