I don't know much about this from the Orioles' end, but a possible reason this deal didn't get done a couple weeks ago is that Mark DeRosa was hospitalized with a heart condition.
You might think that was a reason to do the deal in that case, but it probably wouldn't play well for the guy undergoing heart surgery to lose his job, while in the hospital. (Trading for a backup in that case would be fine, but not someone to take DeRosa's job).
Now that DeRosa seems okay, they could do the deal, but Orioles' backup Freddie Bynum is dinged up. Our most recent update says that a deal before the season starts is unlikely for that reason, but I can't imagine Bynum's injury could really hold it up.
The Orioles have no chance in a stacked AL East this year where even Toronto and Tampa Bay are fielding far better teams, while the Cubs have a huge payroll and are committed to winning now. This is a natural fit, so I'd probably take even money that Roberts is a Cub before Opening Day. (In theory, that is - not opening up the RW sports book with this post). DeRosa's seen more as a supersub than a starter, and it probably comes down to what it would take to get Roberts. I'd imagine Eric Patterson and Sean Marshall would be fair. Maybe the O's would prefer Sean Gallagher. Just speculation here, but there's a good fit.
Of course, the Cubs might want to make a move for a center fielder, too, if Felix Pie (once his nuts are back to normal) can't convince them he's ready.