The next deadline to apply for the Chicago Weekend MBA program is May 10, 2013. If you are aiming for this deadline, you should wait no longer: start working on your essays, resume and recommendation letters. 

The Chicago Weekend application is not a complex one.Here’s a quick analysis of the first two essay questions:
Essay OneHow will an MBA from Chicago Booth – the Evening MBA and Weekend MBA programs specifically – at this point in your life help you achieve both your short-term and long-term goals?
Analysis: These are the standard “Why MBA,” “Why Chicago,” “Why Evening” questions. Briefly describe your career goals, and tie them to the skills and experience you will gain at the Chicago Weekend Program. You want to go beyond generalities such as “improve my financial skills” or “enhance my leadership style”; try to include deep thought about the challenges in your career and what you need to overcome them. 
Essay TwoWhat is the most significant personal or professional challenge you have faced, and what key learning have you taken away from this experience?
Analysis: When answering this question, be careful to balance the story itself and the learning. Applicants tend to spend a lot of words on the details of the story and the set-up, leaving a mere one or two lines for the learning. To my mind, the Admissions Committee mostly wants to see your reflection on the story, what went well, what could have been done better, and how you have changed. Try to show Chicago’s Admissions team that you have acted upon your learning: if you have an example of that, you can incorporate it into the essay.