Jake Peavy, Jesse Crain, Matt Thornton, Matt Lindstrom, Dylan Axelrod, Brent Morel and David Purcey should all be traded before the July 31st deadline, likely for prospects who won't reach the Majors until September of 2014 or later.
Paul Konerko will likely retire.
If no relevant free agents are signed in the off-season, which is entirely possible, then this could be the opening day 25-man roster:
Lineup - 1. Alejandro De Aza CF, 2. Gordon Beckham SS-2B, 3. Alex Rios RF, 4. Adam Dunn DH-1B, 5. Dayan Viciedo LF, 6. Andy Wilkins 1B-DH, 7. Josh Phegley/Tyler Flowers C-DH, 8. Conor Gillaspie/Jeff Keppinger 3B, 9. Alexei Ramirez 2B-SS - at least until Carlos Sanchez is Major League ready. Trayce Thompson should eventually displace one of the outfielders, probably Rios.