We Take "Super" Seriously


We want the best for you and the best from you

Why should you become a Chicago Super Sitter? We know what makes a babysitter great and what makes a great babysitter happy. Not only do we know how everything works, we know how hard the job can be. We expect a lot from our sitters, and that’s why we’ve got your back. We give advice when you need it, we help nurture your strengths, and we make sure you feel like a valued part of our team. We screen each family before you meet them and then provide you with a detailed profile. There are no surprises when you walk in the door. We match our sitters to families based on personality, parenting style, location, and schedule needs.  

1. Submit your Application

We review it and if we like what we see, we contact you directly.

2. Phone Interview

We schedule a call and if we like what we hear, we keep you moving forward.

3. Reference Check

We ask for a minimum of three recent childcare references and one professional reference. And we definitely check their validity. All check out? You keep going.

4. TWO In-person Interviews

We want as many perspectives as possible. You will meet in-person with another CSSitters staff member and if that goes well, you meet with Tori. If she thinks you have what it takes, we’ll keep things moving.

5. Background Check & CPR Validated

These are non-negotiable and must be completed before you start working.

6. Officially Become A chicago super sitter

Once everything checks out and if we feel you meet our standards, we invite you to join the team and get you working!


Please understand that although being a babysitter includes lots of giggling, blowing bubbles, and peek-a-boo, we take our screening process VERY seriously. As we have said, our reputation relies on our caliber of sitters, and we will only work with the best.

Want to be a Super Sitter?

  • Do you have at least three years of professional childcare experience?

  • Do you have exemplary childcare and professional references?

  • Do you work hard?

  • Do you want to be part of an incredible Chicago family?

Become a Super Sitter


What’s the pay and how does it work?
You will be paid directly from your client family at the end of each placement. Your hourly rate will vary from family to family. You can see the rates HERE. You and the family will know this rate before you accept a placement.
How much will I know about the job before I arrive?
When a family signs up with CSS for the first time, they are asked to fill out a form that outlines who makes up the family and how you will be expected to handle the children while they are in your care. We also talk to them, ask a bunch of questions, and vet them before their first placement. We will make sure you have all of the information you need to feel fully prepared.
Who are these families and what are the kids like?
We understand how nerve-wracking it can be to walk into a new home, be faced with new rules and expectations, and have no idea what they actually want from you. Never have that worry again! Before you are placed in a new home, we will send you as much information as we can about the family including discipline style, bedtimes, age-appropriate tantrums or freakouts occurring as of late, demeanor of the parents, and so on. We want you to go to the placement feeling confidently prepared and able to do your best job.
What will be expected of me when I get there?
There is a suggested 15-minute minimum parent/sitter overlap so all questions can be answered and to ensure the kids feel as comfortable as possible. We expect you to use this time to ask questions of the parents, engage the children, and do your best to make sure the parent(s) are feeling ready to leave you in charge.
How does scheduling work?
You are not required to work a certain number of hours to stay on our active roster. We know you have a life outside of sitting and will need some weekends off, but sometimes you will want to work every night possible! In a show? Friend in town? Mid-terms? Can’t work for a while — no problem. Flat tires, lots of bills, in a ton of weddings, or want to work as much as possible? Fantastic! Simply make sure your scheduled availability is up to date. We operate with Google Calendar, and you will be expected to do so as well.
How often will I be placed?
Ideally, as often as you would like. Your schedule is up to you and you’re in charge of maintaining your availability calendar.
You will work your first placements with our long-time Super Families. We collect their feedback — parents AND kids, to be sure they too think you are a SuperSitter.
Why don't I just give the family my number and let them contact me directly?
Our system is based on trust. We expect all sitter requests to go through CSSitters’ booking system and ask our sitters to send the families to us if contacted directly.  If we find out that a sitter is booking CSSitters families without our knowledge they will be removed from the active roster.
Nanny Cams?
With the new fancy technology in our world, nanny cams now come in all different forms. Security system cameras, baby monitors, programs on phones, and the tried and true, hidden ‘teddy bear eye’ camera. These cameras can be a great tool for parents so that they can monitor what is going on with their kiddos when they aren’t home. Chicago Super Sitters asks that families tell sitters if and when recording devices are in use. We firmly believe that these tools are best used as a method of prevention. ‘An ounce of prevention is worth a pound of cure’.