The sentence I’m given:
What I did with it:
Still very clumsy. How do you cite both the New York Underground Film Festival and the Chicago Undeground Film Festival without sounding clumsy and redundant? And I’m not at all sure about the final “s.” I have a feeling including it is more correct, but doing so sounds pedantic and over-formal.
Any suggestions will only be better than what I’ve come up with.
Stick with the first sentence.
Of the two, the first is better.
Or:
… at Underground Film Festivals in NY and Chicago.
Could you eliminate the 2 "the"s in the first sentence? (Well, and spell underground correctly!;))
Winner of “Best Feature” Award at both New York and Chicago Underground Film Festivals.
Reads more like a headline than prose, but I don’t know your context here.
All good thoughts.
I think it’s unavoidably clumsy though; i’ll just find a least evil and move on. Thanks peeps.
That does seem a better way to convey two festivals both called/referred to as Underground.
lissener, are you supposed to be using this forum for homework? 
(I kid, I kid…)
How about “Winner of Best Feature at the New York and the Chicago Underground Film Festivals.”
Festivals has to be plural.
You guys will just have to take my word for this, but I intended to suggest exactly the same revision as Exapno’s.
So, seconded.
I’ll dissent from the majority here. Those are the official names of the festivals, not just descriptions. You don’t factor out redundancy in proper names (except for members of the same family).
It seems wordy, but it’s most correct to say:
*Winner of the Best Feature award at both the New York Underground Film Festival and the Chicago Underground Film Festival. *
“…at both the New York and Chicago Underground Film Festivals”
Yes. This. They’re the proper names of the festivals.
Alphabetical order is a good shield:
“… at both Chicago and New York Underground Film Festivals.”
No apostrophes since the names don’t have it.
Or, alternatively, both go with the full name. But Chicago first (alphabetical order).
If it’s some sort of listing of awards, the first sentence is ok,
otherwise can try …
Winner, Undeground Film Festival “Best Feature” Award - Chicago and New York.
I like the first sentece but without the second “the.” In other words…
“Winner of “Best Feature” Award at both the New York and Chicago Underground Film Festivals.”
Giving proper names in full is usually a good idea and to be preferred. But it does all come down to context. In a less formal context combining long names that get unwieldy is also usually permissible.
This thread is a good example of why authors and copyeditors are natural enemies. There are never “right” answers and context is in the eye of the beholder.
Although I would go back and change even the sentence I suggested after listening to all you others.
I do this stuff for a living, and I’d go with:
“Winner of the Underground Film Festival Best Feature award in both Chicago and New York.”
or, more informally,
“Named ‘Best Feature’ at the Underground Film Festivals in Chicago and New York.”
It kind of depends on how picky you want to be about using the official name of festivals. Generally, IMHO, if using the exact name leads to an unwieldy sentence, don’t use it.
You could even say “the Underground film festivals in Chicago and New York” - lower-casing “film festivals” shows that you’re not using the official name, but “Underground” should be enough to identify which festivals you’re on about.