I'd look to apply early next cycle and really start hammering down for the June LSAT. I see very few people who don't regret having applied a bit earlier at the expense of (hopefully) a much higher LSAT score.

Are you considering Northwestern ED? Seems like you would be a really good candidate, especially if you're interested in Chi. and are debt averse. They'd appreciate all years of work experience more than most schools as well I'm thinking :)