Why work with a babysitter agency?

It's easier, safer, with less BS

Yep, it costs more than doing it yourself. 

But what does your time cost? What does your safety cost?

Families, you pay placement fees and sitters, you pay a small membership fee because Chicago Super Sitters works for you. We do the posting, the interviews, the phone calls, the scheduling, the rescheduling, the background checks, the cancellations, the ‘but are they vaccinated?’ and the ‘but what about my cat allergy?’.

We also make sure they (sitters and families) are who they say they are.


Chicago Super Sitters does the work and the safety checks.

Sitters, an agency should make you feel respected and appreciated.

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. Our flat monthly membership fee is the cost of just one hour of work at $20/month.  It’s meant to keep us hustling for you, and doesn’t change no matter how many hours you work.

Freelance babysitting can be tough. The constant messaging, the cancellations, the awkward money conversations, the last minute changes, the surprises, and not being given all the info you need to do your best job. 

Super sitters handles all of this for you.

        • We assign rates to your gigs so there is no negotiating or haggling (starts at $20/hour)
        • You list availability, we find you gigs that match it
        • We match you to families based on your experience, location, and skills
        • We share info about the family before you arrive, INCLUDING feedback from previous sitters
        • We have cancellation fees in place to protect your income
        • We support you, are here to answer questions, and provide advice
        • We are inclusive AF and we do not tolerate discrimination of any kind. ANY kind.
          Want to learn more?

Working as sitter should be easier. Good news: working as a Super Sitter is easier.

Become a Super Sitter!

Families, an agency should make you feel comforted and supported.

We know that hiring someone to work with your kid(s) in your home is a very big deal. We will listen to you, answer your questions, share best-practices, and set you up for success with any new sitter. We are asking you to trust us, so we work to earn it.

The childcare search can be tough, especially for part-time/occasional bookings. The searching, the ghosting, the last minute changes, and ‘holy swearword you’re cancelling the morning-of?’.

Super sitters handles all of this for you.

        • You and your sitter know the hourly rate before the gig starts – this means no gray area or confusion
        • Once you complete your profile and intake call, your work is done
        • If a sitter cancels, we find an appropriate substitute
        • We match sitters to you based on their experience, location, and skills – not JUST availability
        • We help you curate a short list of favorite sitters to see again and again
        • We share info about the sitter before they arrive so you and the kid(s) know who you are meeting
        • We are inclusive AF and we do not tolerate discrimination of any kind. ANY kind

Booking a sitter should be easier. Good news: booking a Super Sitter IS easier.

Become a Super Family!

Hear what Families and Sitters have to say:


Even when things aren’t Super..

It was awesome knowing someone was there to support me if any tricky situations arose with the family. My placement didn’t end up meeting my needs around covid safety and it gave me such peace of mind to know that you were there to back me up and help me gracefully transition out of that situation.

Sitter 2020

Highly recommend!

We had a challenging group because of the age differences (ages 8,5,2) but (the Super Sitter) was great and was able to figure out appropriate activities for all of the kids for the duration of the summer. We were very happy with the sitter, as well as the CSSitters staff, who all responded quickly and professionally to all our questions and needs. We highly recommend CSSitters to all our friends!

Super Families in a Sitter-Share
Summer 2020

I wish we lived here!

(The sitter) is sunshine. I was nervous that my son would have a difficult time when we walked out the door, and he didn’t even react when I said goodbye. She has such a calm demeanor that couldn’t have been a better fit… for both my kid and me! When he woke up this morning, he immediately told me that he had fun with her. If only we lived here… she would be our #1.

Hotel SuperFamily 2017
Very first online sitter

Long-time Sitter

Consistent flexibility, realistic expectations, super fun.  I love being a SuperSitter.

SuperSitter since 2012
worked with more than 75 CSS families

I just love CSSitters!

CSS embodies much of what I love about working environment: woman-owned and operated, constantly looking to grow and learn, support for both employees and clients, forward thinking and inclusive. I could go on. Working for CSS provides me an opportunity to do something I enjoy while also feeling good about the company I’m a part of. 

SuperSitter in 2014/15, again in 2017

‘Another great experience!’

(The Super Sitter) was very communicative, patient, and warm. They were also very professional. As usual, we had a positive experience with another CSS sitter.

Super Family 2019-2021
First post-Covid placement experience

Thank You!

She was so patient and attentive to my son, who can be a handful. He loved spending time with her, and we were completely comfortable leaving him in her hands. She was up for his creative play ideas but still able to set boundaries with him in a respectful and positive way. Great sitter!!

SuperFamily since 2014
two kids

AirBnB SuperSitter

(She) was great! I really appreciated her quick responses to our texts and how nice and tidy she kept the Airbnb we were staying at.

AirBnB SuperFamily in 2019
bitty baby kiddo, first time with a sitter


I was apprehensive about leaving my little one, especially being brand new to the city. Tori made the process easy peasy! She could not have picked a more perfect sitter. Our son took to his new friend immediately and it was as if we had known each other for a while. I will continue to use Chicago Super Sitters, and I recommend them to everyone. I am beyond pleased with their services and communication. I wish I could give 10 stars!!!

SuperFamily since 2014
via Yelp

Overnight SuperSitter

Oh my goodness, my daughters loved (the sitter)! When i got home from a 2 day trip, she was happy to see me but really just wanted me to go to work so she could have the sitter all to herself. My other daughter was at school so didn’t spend as much time with (the sitter), but did ask if she could come on a weekend sometime so she could spend with her. I really liked her as well. She was great with the girls, down to earth, very comfortable to be around. Thank you for what you do! Your service gives me peace of mind when I travel.

SuperFamily since 2015
Two kids, lots of work travel for mom and an irregular schedule for dad

Stellar Reputation.

I loved working for a company with such a great reputation. I heard from many parents that every sitter they had was great. The few times my path crossed with other super sitters, I was always impressed. CSS also treated me as a sitter very well. I felt the rules were clear and fair. The thoroughness of the placement details got rid of any anxiety I had about the safety of entering a stranger’s house. The info was extremely helpful for knowing how to engage with specific families. And I felt that if unexpected issues did arise (payment problems, etc.) that CSS would have my back.

Super Sitter, 2017-2020

Love the support!

I loved the families, the kids, the service, and the support from CSS – gosh please don’t lose that. It feel great to know someone has your back

Sitter 2019-2020

Long lasting relationships!

I ADORE you all. I look forward to coming back when the time is right. You all work so hard, and I have been able to stay afloat financially because of you, as well as make great connections with families. I am SO grateful.

Sitter 2018-2020
(and will be back!)

Stress Free

We are very thankful to have found Chicago Super Sitters. You have made our transition from no babysitter to several babysitters wonderful! My son absolutely loves both sitters that you have placed with us and we are excited to have them come back. Thank you for making this experience stress free and anxiety free.

SuperFamily in 2019
Toddler mom, quick to be a regular family

Loved her!

(She) was a fantastic sitter! She was warm, friendly, and courteous, and our girls immediately warmed up to her. I was especially impressed at her effort to get to know & connect with each of our three girls, and how positive & kind she was in her interactions with them (and us!). We would love to have (her) back whenever she is available to babysit. Thank you so much for another great sitter!

SuperFamily since 2015
Three busy kids

I love all of my Sitters!

As usual with CSS, this new sitter was great! She really had great energy, and even got my son to nap! I can’t say enough wonderful things about CSS, and (this sitter) is just one example. I’d love to have her back!

SuperFamily since 2014
toddler kiddo, lots of different schedule needs

I absolutely loved working with CSSitters!

I knew that any family I was about to meet was going to be organized, kind, and thoughtful to the sitter. I loved the set up of having a “membership” with CSS and being able to gig when I wanted to, or had more time. This was a supplemental income for me, and it worked so well.

Evening & weekend Super Sitter

Fur-babies too!

I just wanted to reiterate how happy we are with all of our sitters and experiences with CSS. You choose wonderful people to represent your company who take care of our kids – including furry babies – with lots of love and patience. We’re so grateful to have found CSS years ago. Thanks for all you do!

SuperFamily since 2014
two kids, very nervous pup

Full and part-time

I now work a full-time job but still remain a sitter for CSS because it is an all-around amazing organization to be part of. Tori’s passion for what she does shows through the thorough intake/hiring process and her ongoing direct support. I love the various kiddos/families I’m able to work with and not to mention the flexibility of making my own schedule and picking up more hours with a moments notice!

SuperSitter since 2017
full-time to part-time sitter

So much flexiblity!

I simply love CSS! The CSS team does an amazing job at pairing sitters with families and each and every time it’s been a great fit! They take the time to get to know each family and each sitter which is why they have such great success with pairings! I love that I can take three babysitting gigs one weekend when I’m free and also not make any babysitting commitments for the following weekend- the flexibility is amazing!

SuperSitter since 2016
works around crazy hospital shifts

You really really saved us!

Honestly, I’m pretty sure our kids would prefer spending time with (the Super Sitter) over us, and that’s 100% ok, ha. After COVID and quarantine – she came into our lives 5 months into both of us trying to work two full time jobs with zero childcare. We were about to pull our hair out and she was a breath of fresh air. The boys talk about (the Super Sitter) when she’s gone, and love to relay stories of the games they played, or the facts they learned during their time with Jess. Honestly, I don’t know how we could have made it through COVID, working from home, while being isolated from all family and social supports without her or CSSitters. THANK YOU SO MUCH!

Super Family since 2016
Covid-frazzled mom, saved by her Super Sitter in 2020


I have been working as a childcare provider for years and I have never felt safer or more prepared going to new homes. Tori is a truly gifted matchmaker of sitters and families and I feel very lucky to be one of her SuperSitters!

SuperSitter since 2014
has worked with more than 60 CSS families

Become a Super Family!

Become a Super Sitter!