Oh did you notice that you posted in probably the wrong place? I suspect an Admin on AN will move your thread for you.
I am not aware of any place at least in Northern IL that utilizes LPNs. Getting work as an RN after graduation will be very tough, no matter what your plans are. Also understand that many facilities will not count LPN experience as a "sort of" RN experience.
Once you enter the RN program it will be tough to find work that fits your schedule from school, which the associated studying, projects and general faculty confusion will not give you something firm to bank on. I'd just do the CNA thing over a summer or something an try that. LPN and CNA pay will be quite low. Most RN programs let you do your CNA or LPN test if you want it after a semester?! I think. So, why spend the extra money to take a separate class.
If you have prior business experience, you might look for medical office admin. jobs. If you can manage to get into night RN classes and then work during the day at your job, you'd probably make more money. But, you have to have a flexible boss, and figure out when you are going to study and do stuff like research papers and care plans.