• Family Planning

    Made Simple.

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  • Domestic Staffing Agency

    Full-time Nanny, Part-time Nanny, Night Nurse, Housekeeper, Personal Chef & House Manager.

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  • Maternity Concierge & Baby Planning

    Services tailored to meet your specific needs.

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  • Education Consulting

    Assisting families with educational decision making
    from preschool through high school.

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  • Event Planning

    Birthday parties, baby shower, gender reveal parties, Baby Naming/Bris, Bar/Bat Mitzvahs.

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Mission Statement

Strollers and Stilettos® is dedicated to providing assistance to busy families in Chicago. We find inspiration in understanding each individual client’s needs and ensuring satisfaction.


Katie Lewis, the enthusiastic and kid savvy founder & CEO of Strollers and Stilettos® began her career as an elementary education teacher and nanny. While working as a nanny and household manager for busy professionals in Chicago, she began to notice a pattern among all of her families: they needed assistance in managing the many aspects that come along with having children. Whether it was the anticipation for the arrival of a baby, designing a nursery, finding the perfect preschool or school, hiring and managing the most qualified nannies, planning that special birthday party, scheduling and managing all appointments, activities, and play dates for kids and family, or personal shopping; Katie got the job done.


Thus, Strollers and Stilettos® was started with a mission to help make families’ lives easier by doing the things they don’t have time for or just might not want to do.


  • "Strollers and Stilettos made my nanny position search easy and enjoyable, and I am now working for a wonderful and professional family in Chicago. Katie responded to my application promptly and... more

    Amy S., Nanny and Educator
  • "I previously worked as a nanny with Katie Lewis. Katie created an exceptionally seamless round the clock nanny schedule, along with delegating household tasks and keeping the... more

    Nicole C., Nanny and Educator
  • "Katie Lewis of Strollers and Stilettos is exceptional. She is professional, intelligent, and extremely responsive. Katie wants to know your kids, even after your initial consultation. She knows... more

    Ashley T., Publishing and Mother of two
  • "Katie Lewis is remarkable - organized, efficient, creative, and laser-focused on quality.  Katie instinctively understands what children - and busy families - need, and her energy and... more

    Barbara H., Senior executive and Mother of two
  • "Thank you for being an excellent resource over the past year. As first time parents, we were anxious and overwhelmed in finding the best childcare for Will. Katie's expertise and insight helped... more

    Amanda L., Director of Marketing, Mother of one
  • "I met Katie about three years ago and I cannot imagine what I would have done without her.  I am a single mom and she has helped me so much.  My son truly loves her!  As she was... more

    Kathryn S., Broker and Mother of one
Call Us: 312.768.8030