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I am preemptively asking this question because I have not gotten my score back (I took September 2014 two weeks ago as my first).
For the purpose of this question, assume I have scored a 160.

I studied for a good few months, but took a full month off and tried to start back in it right before the test. It was a combination of a medical condition followed by feeling sorry for myself. Not only am I not content with a 160, I don't think it showcases my potential nor does it give me any level of leverage on paper.

My question is should I apply now with this score (note my gpa) or should I risk working to a higher score in February and apply?

In both scenarios, I would be applying for Fall 2015.

To start off I'll give some basic information.
Graduating Undergrad FALL 2014 (December I will be done)
GPA: 3.0 <<<I know, just writing it out made my stomach crawl.

Goals:
-Attending Law School Fall 2015
-Not necessarily a T1, but a top 50 (preferred in Illinois/midwest, but will move for enough money)
-Hitting as high of an LSAT score as possible...
>My best was a 165 but it was not in the most optimal condition (I think I let myself get 2-3 minutes extra on RC);
>Best not "cheating" was 164
>That being said, average was 160
>Week before test I got a 162 in real test conditions (test center, unexpected construction next door, proctor, full breaks, the whole sha-bang)

You know you can retake in December right?

3.0 undergrad GPA and a realistic LSAT of 160 or so?

Is there anything else you might be able to do with your life? I'm not trying to be snide; it's a legitimate question. Your numbers are not promising in terms of A. attending a law school with solid job placement and B. at a price that leaves you with a manageable debt load.

If law school is the only desired path you wish you take, the vast majority of posters on this message board - with good reason - are going to recommend either quitting the law school dream and re-analyzing yourself, or getting your LSAT to a 170+. Probably a 167-ish at a minimum.

Have you spent time researching Law School Transparency and Law School Numbers? If you haven't, I strongly suggest you do.

A 3.0/160 is not going to create any options that are workable for essentially anyone's goals, and I'm probably one of the posters most amenable to 0Ls attending non-peer schools. You're going to need to do better on the LSAT, and if you want to go in 2015, you'll need to do better on the LSAT this December, instead of February.

What are your goals and what's your career/life background? Why must you attend in 2015? Sounds like an all-around terrible idea with what you have provided us.

What everyone else said, plus, if you wait out this cycle, you still have an opportunity to actually improve your GPA before you graduate, especially if you take A+ classes which can heavily increase your GPA.

Once you graduate that window is closed and you'll forever be boxed out of many schools regardless of how you do on the lsat, softs, etc.

You'll need a 170+ with that GPA.

That being said, I know people who retook in February and got into HYS after that. But not with a 3.0 GPA.