The most direct route from Sioux Falls, SD to Hillsdale, MI covers ~510 miles (820 km) and takes 8 hours 10 minutes in ideal conditions.
I-90 E (Sioux Falls) → I-29 N (brief) → I-90 E → I-39 S (WI) → I-43 S → I-94 E (Chicago bypass) → I-69 N (Fort Wayne) → US-127 N → Hillsdale.
Alternative: I-90 E all the way to I-80 E → I-69 N. Similar time, more tolls (Indiana Toll Road, Ohio Turnpike).
Hillsdale College and the surrounding area are the main draw. Fuel up in Indiana (cheaper than IL/MI).