Trade doesn't make sense for any of the three teams, really.
For Portland: firstly, Aldridge and Boozer both are power forwards; Aldridge is not going to play center (which is why the grossly undersized Hickson had to play center last year) and Boozer just isn't a center. Beyond that, Portland's issue wasn't with its starting roster; it was with their bench, which was the worst in the league in terms of production last season. What'd they do this summer? Flesh out their bench. This trade would gut them of all of the depth they just worked to acquire this summer and place them right back in the position they were in last year: a lottery team with a bad bench.
For Chicago: with Rose's injury, the new goal is going to be cutting costs to avoid incurring the repeater tax. Acquiring Rondo and Bass doesn't help with that.
For Boston: I just don't see the point in acquiring a bunch of young players playing exactly the same positions as the young players currently on the Celtics. There'd be a lot of duplication, which would inevitably stifle their individual development.