I teach in the School of Education at DePaul University. I really think this is an excellent program to go through. Almost all of the graduate students are career switchers (from the corporate world). It would be almost pointless to get another bachelor's degree in teaching b/c the pay will be low. Your best bet is getting a Master's. UIC, Roosevelt, Northeastern, and Erikson also have programs in the city. DePaul is great b/c it really focuses on preparing Urban Educators. Once you finish your program you would have a Master's degree and an Illinois Teaching Certificate.
Another route is to do a direct-entry program where you teach during the day and get paid and go to school at night. These programs look appealing but I caution you...they aren't always as highly respected as traditional programs.
There are plenty of jobs in the city!! You'd be able to find a job pretty easily once you finish (about 2 years).
I will caution you--teaching is not an easy job. While it seems you'll have an easy schedule and a lot of time off; you'll have to do a lot of work outside of the job, especially in the first few years. I'm not trying to discourage you. I just want you to know the facts before you pursue a degree and complete life change.
Please e-mail me if you'd like to learn more. I've been teaching education courses at the college level for a few years and I can give you some more advice if you need it.