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
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.