I know 2 families in the South Loop that found their babysitters through Craigslist. I've also heard recommendations for sittercity.com, but they charge a fee for using that site.
Another possibility might be to find someone through one of the colleges in the area, though their schedules might not meet your needs? My current babysitter is a recent graduate from DePaul University, but she is job searching now and won't be available during the days as soon as she finds a job.
I would use sittercity.com, I never had to pay a fee (the extra fee is only if you want to get a background check on the person you may want to hire, etc). I'm an inhome nanny and this is how I usually receive my jobs, I wouldn't always trust craigslist and do make sure you try and get a background check which is great with sittercity since you can pay a fee and have it done through the site easily.
I used to be a nanny and would recommend sittercity or care.com. There are so many caregivers on both sites and you are able to look at a lot of information about them even before first contact. You can either look at the existing profiles or you can list the job that your family is hoping to fill.
Re: Finding a babysitter
I know 2 families in the South Loop that found their babysitters through Craigslist. I've also heard recommendations for sittercity.com, but they charge a fee for using that site.
Another possibility might be to find someone through one of the colleges in the area, though their schedules might not meet your needs? My current babysitter is a recent graduate from DePaul University, but she is job searching now and won't be available during the days as soon as she finds a job.