
"Katrina watched our son while we were in town for a wedding. She was timely, so nice and sent great pictures throughout the evening. He looked like he was having more fun than we were!"
Madeleine B., parent

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Families in Chicago turn to UrbanSitter for wedding and special event babysitting.
117 available tonight | Avg hourly rate: $22.63/hr
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Hi! My name is Dria and I am a college student studying in downtown Chicago at Roosevelt University. I am living in an apartment in Pilsen, and am available to work anywhere accessible by CTA! I am CPR and First Aid certified! I have 6 siblings, 3 of them being younger than me (2, 6, and 10 years younger!) so I have a lot of experience with kids of all ages. I have done a lot of summertime babysitting for family, friends, and more. I also worked as a Camp Counselor at a children’s summer camp! I can cook, clean, and of course ensure that your children are in a safe, comfortable, and fun environment!
I think of life as one great adventure, whether it be exploring the outdoors or taking an exotic journey via a good book. I have been teaching in Chicago Public Schools for 19 years, plus taught theater, gymnastics, and dance for 13 years at private studios before entering the school system. When not in the classroom you can find me running the streets of Chicago, cuddling with my cats, hiking canyons, eating chocolate, wandering art galleries, climbing mountains, catching a broadway show, snowboarding, or lost in thought at the museum. Happy to watch kids in a single setting or take them on an unforgettable adventure.
Hi! My name is Hailey I graduated from Columbia College Chicago in the fall of 2024. I live in Streeterville so I don’t drive but I’m willing to commute/ have experience ubering with kids. I’m a model and actor full time, so babysitting/nannying is how I fill my free time! I have 7 years of childcare experience. I worked as a camp counselor at YMCA back in Dallas Texas (where I’m from) in 2020. I realized I loved working with kids and started working for a babysitting agency when I first moved to Chicago in 2021. I have children I’ve watched since they were newborns that are now about to start pre school. I have children I’ve known since they were in elementary school entering high school. I love working in childcare and helping where I can! I remember all of my babysitters from when I was a kid. My goal is to make sure that I leave a positive mark on the extra childhood memories of every child I watch. I want to make sure that the kids have fun, feel safe, and grow. I went to art school, so I’m very creative. I love all pets! I love tidying up and I’m ok cleaning when needed as long as it’s discussed. I have a pretty open schedule and am available for last minute care. Just let me know how I can help and I’d love to!
“It was an absolute pleasure having Hailey in our home. She established a connection with our children very quickly, all while allowing them to naturally adapt. She kept them active and engaged for the full time she was with us, mostly using imaginative play. Highly recommend. ”
Hello! My name is Hannah, and I’m currently studying Public Health at the University of Illinois at Chicago. I am also an assistant preschool teacher. I have a passion for traveling, reading, and trying new foods. I’ve always loved working with children and have years of experience caring for infants, toddlers, school-age kids, teens, and children with varying abilities. My background includes working closely with children with disabilities, and I pride myself on creating a nurturing, inclusive environment for every child. In addition to childcare, I’m happy to assist with household tasks such as cleaning, cooking, and running errands to help make your life a little easier. I’m excited about the opportunity to provide dependable and compassionate care for your family!
Hi I’m Jordan! I double majored at Purdue in psychology and law & society and graduated in 2024. I moved to Chicago for law school and I am in my third year. I have been providing childcare since I was about 16 years old and I’m first aid & cpr certified. I worked at a local daycare in my hometown for a summer. I was also a nanny my senior year and continued to nanny for that family until I left for college. While at Purdue, I worked at a daycare. I was a floater, so I worked in the infant room, multiage room, 2s room, and pre-k so I am comfortable with all ages! I am also comfortable with pets!
“Jordan is wonderful! She is kind, professional and timely. She was great with our 1.5 year old, and we highly recommend her!”

As of November 2026
Every babysitter on UrbanSitter completes an annual background check, and every profile is individually reviewed by our Trust and Safety team.
847 sitters background checked in Chicago, IL
4.9 average star rating from 4,857 reviews in Chicago, IL

"Katrina watched our son while we were in town for a wedding. She was timely, so nice and sent great pictures throughout the evening. He looked like he was having more fun than we were!"
Madeleine B., parent

"Caitlin was awesome and jumped right in to chaperone four girls (10, 9, 8 and 6) at a family wedding (they were bridesmaids) and she was very helpful with the event as well as taking them home and putting them to bed."
Lila P., parent

"McKenna was great with our 3 year old son! She came prepared with a box of fun activities and handled playing, dinner, and bedtime seamlessly... and it was all at our hotel while we were in town for a wedding. Thank you McKenna!"
Catherine B., parent

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Browse profiles and read parent reviews for free.
To sign up with Facebook, we need permission to use your email address.
Sharing your friends list is optional, and allows us to connect you with sitters they book and recommend. Nothing will be shared or posted.
Share the wedding date and babysitting details, then hear from available sitters. Review your options and hire only if you find the right fit.
Browse profiles, read reviews from other parents, and pick the babysitter you feel best about. No agency assignments.
Every babysitter completes an annual background check. See bookings, repeat families, and reviews from local parents.
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