How to Choose a Daycare or Preschool in Chicago: Questions Every Mom Should Ask

Hi everyone! When talking to moms of newborns in Chicago, one of the most common topics that comes up again and again is how to find the right childcare program for our little ones. We both LOVED our daycare/preschool programs, so to answer these questions, we thought we’d go straight to the source. 

Lucie’s son went to The Gardner School for daycare for 4 years, and loved it! So we sat down with their team to answer all of your questions about choosing the right daycare and preschool in Chicago - whether you go here or otherwise.

First day of daycare at The Gardner School

(And if you do decide The Gardner School is the right fit for your family, mention Friend of a Mom - they are waiving all registration fees for our moms!)

How to Choose the Right Daycare or Preschool in Chicago

Choosing childcare is a big decision, and it’s completely normal to feel a little overwhelmed at the start. You’re thinking about your child’s safety, their happiness, their development, and who you’re trusting to be part of their daily life. That’s a lot to hold, especially when every option seems to promise something different.

Starting with the right questions can bring a sense of clarity to the process. When you take the time to understand a school’s approach, how teachers connect with children, and what a typical day really looks like, you begin to see what will truly support your child and your family. That effort upfront helps you move forward with confidence.

And that confidence carries you through the years ahead. When your choice feels aligned, your days feel smoother, communication feels natural, and you can focus on what matters most: watching your child grow, learn, and feel right at home.

When to Start Looking

Starting your search early can make the process feel much more manageable. For infant care, many families begin touring schools during pregnancy or shortly after their baby arrives. This is a helpful time to ask how waitlists work, how far out programs are enrolling, and what timing realistically looks like for your ideal start date, especially since care for children as young as six weeks can fill quickly.

For preschool, typically ages two to five, beginning your search six to twelve months ahead of your desired start date gives you time to explore, ask thoughtful questions, and feel confident in your choice. In cities like Chicago, where families are often balancing full schedules and commuting, timing and location can play a big role in availability.

Each neighborhood and school operates a little differently, so understanding timelines early, staying in touch with programs you love, and keeping some flexibility as you explore can help you find the right fit at the right time.

Types of Childcare Options 

There are several types of childcare options to explore, and each offers a slightly different experience for children and families. Daycare centers often provide full-day care for a range of ages, with structured routines, social interaction, and a team of educators supporting your child’s day. Preschool programs typically focus on ages two to five, with an emphasis on early learning, independence, and preparing children for the transition to kindergarten.

You may also come across different educational approaches, like Montessori or play-based learning. Montessori classrooms are often more self-directed, while play-based programs center around exploration and creativity. Many toddler through Pre-K childcare programs blend the two ideas, combining teacher-guided learning with hands-on play. This approach helps build early academic skills while keeping children engaged and confident as they learn.

Key Questions to Ask When Touring 

Daily Structure and Environment

Ask what a typical day looks like, including how time is balanced between learning, play, rest, and transitions. You can also ask how classrooms are set up and how children move through their day. Listen for a thoughtful rhythm that feels predictable but not rigid, where children have opportunities to explore, engage, and recharge. A well-designed environment should feel calm, organized, and intentionally set up for different types of learning and play.

Teaching Philosophy

Ask how the school approaches early learning and how teachers support both academic and social development. It’s helpful to understand how the curriculum is introduced and how children are guided through new skills. Listen for a clear, consistent approach that blends teacher guidance with hands-on learning. Strong programs will be able to explain not just what they do, but why it matters for your child’s growth and confidence.

Staff and Consistency

Ask about the teaching team experience, training, and how long staff tend to stay with the school. You can also ask how classrooms are staffed throughout the day. Consistency is key in early childhood, so listen for answers that reflect stability, strong relationships, and support for teachers. When educators feel supported, it shows up in how they connect with children and families.

Communication and Safety

Ask how the school communicates with families on a daily and ongoing basis, as well as how they handle safety, health, and emergencies. Look for clear, proactive communication and systems that help you stay informed and connected. Listen for communication that feels like a partnership, not just updates. When it comes to safety, listen for detailed, confident answers that show preparation, transparency, and a genuine commitment to every child’s well-being.

As you tour, pay attention to how the space feels. Do teachers engage naturally with children? Do you feel welcomed and comfortable asking questions? Those small moments often tell you just as much as the answers themselves.

Questions Parents Don’t Always Think to Ask

What happens when a teacher is out for the day?

Consistency matters more than most parents realize. This question helps you understand how classrooms are supported day-to-day and whether your child will still see familiar faces, even when schedules shift.

How do you support children during transitions throughout the day?

Transitions can be a big part of a child’s experience. Thoughtful support during these moments helps children feel secure, confident, and ready for what comes next.

How do you handle different learning styles or developmental paces?

Every child grows in their own way. This question helps you understand how teachers adapt and support each child as an individual.

What does a great day look like here for a child?

This invites a more personal answer and gives you a window into what the school truly values in the daily experience.

How do you handle days when a child is having a hard time?

Every child has off moments. Listen for how teachers respond with patience, connection, and care in those situations.

How do you partner with parents beyond daily updates?

Communication should feel like a relationship, not just a report. This helps you understand how the school keeps you involved and supported over time.

How does your approach hold up on a busy or unexpected day?

Schedules shift, teachers are out, and children have unpredictable moments. This question gives you a clearer picture of how the school maintains quality and consistency in real, everyday situations.

How do you handle parent concerns or feedback in real time?

Look for open, responsive communication and a clear plan for follow-through. You should feel heard, supported, and confident that concerns are addressed thoughtfully and in a timely way.

Common Mistakes Parents Make

Prioritizing location without fully understanding the classroom experience

Convenience matters, especially with busy schedules. Taking time to look beyond location helps ensure the environment, teaching approach, and daily experience feel like the right fit.

Assuming “no news is good news”

It’s easy to feel reassured by simple daily updates. Asking for clear, ongoing communication helps you stay informed and avoids surprises down the road.

Not digging into how the school operates on a typical day

Tours highlight the best moments. Asking how classrooms function during transitions, staffing changes, or busy days gives you a more complete picture.

If possible, talk to the teachers to get a sense of their energy, engagement, and overall happiness. That day to day experience often reflects how supported they feel and directly impacts your child’s experience.

Not fully reviewing policies that impact your daily routine

Details like illness guidelines, hours, and enrollment expectations can shape your experience. Understanding these upfront helps avoid unexpected challenges later on.

Choosing based on what worked for another family

Every child and every parent is different. What works for one family may not work for another. The best choice is the one that aligns with your child’s personality and your day to day needs.

What Actually Matters Most

A high-quality program is built on consistent, caring relationships. Children thrive when they feel known, supported, and comfortable in their environment. Experienced teachers, a thoughtful daily routine, and a balance of guided learning and play all work together to create that foundation.

What matters most is how your child feels each day. Do they feel safe, engaged, and excited to be there? Are they building confidence, forming friendships, and growing at their own pace? When those pieces are in place, everything else tends to fall into place, too.

Final Thoughts

Finding the right childcare option takes time, thought, and a little patience, but it’s worth it. As you explore, ask questions, trust your instincts, and give yourself space to find what feels right for your family.

When you find a place where your child feels comfortable, supported, and excited to learn, you’ll feel it. And once that foundation is in place, you can move forward with confidence, knowing your child is exactly where they need to be.

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Gardner School Perspective

At The Gardner School, we focus on creating a consistent, supportive environment where children feel known, cared for, and excited to learn each day. Our programs are thoughtfully designed for each stage, from infancy through Pre-K, with a balance of structured learning, play, and social development. We believe strong relationships, experienced teachers, and a clear daily rhythm make all the difference.

Our approach blends teacher-guided instruction with hands-on, play-based learning, so children build early academic skills while staying engaged and curious. Classrooms are intentionally designed to support exploration, confidence, and independence, while still providing the guidance and reassurance young children need.

Families are an important part of the experience, and we prioritize clear, ongoing communication and a true partnership with parents. With a focus on consistency, quality, and connection, we create a safe environment that supports children today and prepares them for all they will become.