hiring nanny chicago


Hiring a nanny in Chicago can seem daunting, but it doesn’t have to be! Here we shares tips for successfully finding your next childcare professional.


Are you a new parent setting out to hire your first nanny in Chicago?

Or maybe you’ve already hired one or two that just didn’t work out. Do wish you could gain just an inch or two of expert insights on the process because you know it would take you the mile?

Well, today your wish comes true! We went straight to an expert who has interviewed hundreds of nannies. Jessica Swartz of Olive You Nanny Agency answers our questions and shares with us her hard-earned nuggets of knowledge about hiring a nanny in Chicago.

Hiring A Nanny In Chicago Q&A

To start, can you tell us about the childcare provider ecosystem in the Chicagoland area?

“We are fortunate in Chicagoland to have great diversity in our nanny community. We have everything from recent college graduates who have decided to pursue a full time career as nannies, to nannies who have been with their families for seventeen years. When a family describes their ideal candidate, we can usually find it in Chicagoland.“

What are the key difference that you find in nannies compared to babysitters?

“We define a babysitter as someone who watches your children on an occasional basis: weekends, date nights, etc. Nannies have a set schedule, more childcare experience, and should be able to provide your family with amazing references. Nannies usually have more household responsibilities than a babysitter as well. “

Are there any uniform qualities to look for in a nanny?

“Your nanny will generally spend more waking hours with your children than you, so you want your nanny to be on board with your parenting style, and be a loving, caring, positive influence for them. Maturity is also hugely key in a nanny.“

What are the warning signs to look out for during the interview?

“As an agency, when we interview nannies, we’re looking for a genuine love of children, and an understanding of the important role nannies play in families’ lives. We’re also looking for someone who is a “career nanny”, rather than someone who thinks nannying might be a fun stop gap between college and their next career move.

“Warning signs to watch for are:

“Immaturity and/or lack of good judgement. Nanny candidates should be able to provide examples of a challenging situation either with parents or children and how they navigated through. Families should also be leary of candidates who are unable to provide glowing references, and candidates who have moved from family to family in a short time frame.”

When there are a few great candidates to choose from, how do you advise parents on how to decide?

“This may sound cliche, but we tell families to follow their gut when choosing their nanny. We believe that you will know your nanny within their initial interview. It may be the instant connection they have with your children, or even with your pet. It could simply be the overall warmth you feel from them.

“We compare it to meeting a significant other: There’s something about them that makes you think, “Yes, this is the person that needs to be with our family.”

“We also recommend scheduling a trial with your top candidates, so you can see them in action, to be sure they will blend well with your family.”

What can parents do to start things off on the right foot?

“Communication is the key to starting off on the right foot with your nanny and the key to maintaining an effective relationship long term. Like any new relationship, there will be growing pains, as both family and nanny get to know one another. If your nanny is consistently putting the milk away on the wrong shelf in the fridge, and it’s driving you batty, let her know!

“It may sound silly, but ignoring little things like that can lead to serious resentment in the long run. For the first few weeks, plan to sit down with your nanny weekly, so you can all review the week and how things are going. This ensures that things are being done the way you would like, and helps the nanny feel that she is valuable and her opinion matters as well. It is also invaluable to have a written agreement of your expectations of nanny’s duties, vacation/sick time, and regularly scheduled hours.”


Thank you so much for your time and contribution, Jessica!

As a parent who didn’t do it right the first time and learned the hard way with our first hire, I suggest you study Jessica’s valuable advice!

Special emphasis on her last point about starting things off on the right foot by putting your agreement in writing. It is too much to keep track of. Proper documentation catches differing interpretations and helps to swiftly rectify misunderstanding when it inevitably arises.

Via The Village offers free nanny and nanny share contract templates. You can download and edit the contract per your unique agreement.

I can say going through the nanny hiring process on your own does not come without a learning curve. When we sought out a nanny, it wasn’t in our budget to go with a nanny agency. But having gone through the process a few times, I’d say if it is within your budget, an agency is worth every cent.

I also strongly agree with Jessica’s point: follow your gut. When you know, you know. If you are looking to DIY your nanny search, check out viathevillage.com. If you’d like to go the agency route, have Olive You Nanny introduce you to your nanny hire!

We wish you success at hiring a nanny in Chicago!