We are looking for a reliable babysitter to care for our 2-year-old son, Ollie, in Chicago, IL. The job starts on Sunday, February 8, 2026, at 12:30 AM and ends at 7:00 AM. Ollie tends to struggle with sleeping without his parents but usually falls asleep quickly when a calm movie is on. The pullout couch in the living room will be set up for his comfort. Snacks will be provided for Ollie, and feel free to enjoy anything in the kitchen. Responsibilities include ensuring bedtime routines are followed and providing comforting presence throughout the night. Free parking is available on the street and surrounding blocks. We will be dining and attending a show nearby but are accessible via text for any inquiries or emergencies during the job. No pet care required as there are no pets in the home.