From Chicago head to the Badlands. Worth a 2-4 hour drive on the loop depending on how much you wish to photograph or hike. Another 11/2-2 hours to Keystone SD and Many highly rated CG's. Rushmore 2 hr+ daytime, visit Crazy Horse Monument then revisit Rushmore for night lighting ceremony, 1 day. Custer State park, Needles HWY and Wildlife loop, 1 day Must see. Devils Tower, set up campsite at wherever you stay in Yellowstone area would be 4th day. Need 1 day for Jackson Hole and Grand Tetons area. Need at least 2 if not 4 days to see Yellowstone. If you walk the boardwalks and see all the features 4 days cover each quadrant. That is 9 days to this point and you really rushed through the Black Hills. If you like Caverns there are a couple in the Black Hills worth touring. Nice Steam Train day excursion in Hill City too. I would consider 2-3 extra days in the Black Hills which would put you up to 12. 3 days return trip to Chicago leaves 4 more days. Wyoming and South Dakota are full of other attractions so you could research extra stuff to do. Spearfish Canyon Drive on a Motorcycle would be Very recommended. I'd go in July or August so weather would be better for cycle riding.