I can probably drive 55 with my eyes closed. I have been making this drive back home to my parents in Sandwich, IL for the past 19 years.
If you hit Rod's Reef in DeKalb on Saturday, I would recommend heading into Chicago on 88 and finding a hotel around Naperville or Downers Grove area. I know there are a number of hotels right off 88 and also some off of Ogden avenue. From here it is not a bad drive into Chicago on Sunday morning.
Also, staying downtown has many perks for a Saturday night. Check Hotels.com and see what kind of deals can be had for downtown Chicago.
There are really no hotels south on 55 until you get around Plainfield.
Just some ideas