Look for the Cubs to outright at least two players this week, possibly more.
Now that the Cubs season is over, C Taylor Teagrden and OF Quintin Berry will very likely get outrighted to Iowa (neither is likely to get claimed off waivers). Then once outrighted, both players will very likely elect to be a free-agent (both are Article XX-D players, Teagarden because he has accrued at least three years of MLB Service Time, and Berry because he has been outrighted previously in his career).
INF Jonathan Herrera is another candidate to get outrighted this week. Herrera would very likely elect to be a free-agent if he is outrighted, but unless his 40-man roster slot is needed right away (it's not), the Cubs will probably wait to drop Herrera frrom the 40 until 12/2 (the date 2016 MLB contracts are tendered).