I think your assumption of the amount of flying you will be able to accomplish in the Chicago area, given the weather patterns, is excessive. Remember, the guy from ATP is a salesman first. His job is to get your money. If Mother Nature doesn't play ball, it's not his fault. So yes, you may well end up doing "repeat" lessons. Which will cost more money.
As others have stated; and I hate to throw another bucket of cold water in your face...you will not be competetive at all with those hours. To assume that just because you have a wet CFI ticket with an MEI attached to it, that someone will let you begin instructing ME students is not a stretch...it's a leap across the Grand Canyon.
Now...the issue of college and degrees. Good idea. Consider this. At respected schools, you will complete a well rounded 141 program with your comm/inst AND an AS degree in two years. You can then take an additional semester and pack in your CFI, II and ME. Armed with those, you will have a better than average opportunity (assuming you are a good stick and decent person) of teaching at the school in their program. Meaning building hours and experience. You can also continue in a four year program with a different discipline. A good example of that is Florida Tech. They have a full plate of various programs outside aviation. So do other schools.
I understand where you are coming from and your desire to go fast. I wanted to do the same thing. I ended up taking a year off between high school and college...a very wise move...and then went full bore at school. Got my 2 year and went back into the schools flight department and racked up 1500 hours in about 18 months, then landed my first regional job at 22. By age 24, I had been a Captain on two different airplanes, with a type in one and got hired by a major at age 24. But I also had 3,800 hours and a lot of turbine PIC.
Times are different now. The push will be for more experience...not just the minimum hours...as has been the trend recently. As far as majors...and by that I also include the big cargo carriers like FedEx, UPS and Atlas... where the real money and growth will be in the coming years...it's going to be experience and hours.
Good luck!