Unless they win 3-4 more cups (or 1-2 with some finals appearances mixed in) they aren't touching the 90's Bulls dynasty. I won't count playoff appearances because I don't feel like looking those up for each team
but I will count finals appearances (cause that is still one of the ultimate goals, winning of course, is the goal) so I'd rank them as..
1990's Bulls (x6 championships)
1940's Bears (x4 championships, x5 finals appearances) x5 championships and x6 finals appearances if you include the Chicago Cardinals
1900's Cubs (x2 championships, x3 finals appearances)
1930's Black Hawks (x2 championships, x3 finals appearances) - you can flip flop both those era's.. only reason I put them below the 1900's Cubs was cause of the '38 team
2010's Blackhawks (x2 championships)
- still pending of course
1920's Bears (x1 championship, x6 finals appearances) x2 championships and x7 final appearances if you count the Chicago Cardinals.
1910's White Sox (x1 championship, x2 finals appearances)
And then you have your one time champions who were a bit disappointing in potential dynasties (60's Black Hawks [and I can't stress them enough], 60's Bears, 80's Bears, and I'll even include the 2000's White Sox in there, although that's very debatable.. sigh) and some who were in the finals more than once, but didn't win it (30's Cubs, 70's Black Hawks)
Now, this is what I grade on
championships and appearances alone which I believe is the most important. If people want to argue playoff appearances, parity in each league, which championship is/was the hardest to get, etc. be my guest.
Oh and kind of OT, but everyone forgets the Cubs and White Sox were basically the kings of baseball in the early 1900s. Great history to look at/read about there.