If you truly are "ORD and bored", you really have nobody to blame but yourself.
First point of order. The Cumberland stop suuuuuucks. As does Rosemont and Harlem.
Go in a little bit deeper; the Jefferson Park exit gives you easy access (via CTA bus) to Lincoln Square, which is a great neighborhood. Head a little bit further east and you'll hit Andersonville. You can find great apartments, great people, great food, great bars.... Set up a crashpad and enjoy the commuter lifestyle for once.
Take the Blue Line a few stops further and you'll hit Logan Square and Wicker Park. A few too many hipsters for my taste, but the eats can't be beats.
Bottom line, of you have to sit in Chicago, don't sell yourself short by limiting your choices to the first 5 minutes of the Blue Line. It's a whole 'nother world just 10 minutes deeper.
And it's even better in the summertime, I assure you!