Paid Time Off Jobs in Chicago, IL

72,501 open positions · Updated daily

Looking for Paid Time Off jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Paid Time Off position in the Chicago, IL area.

Chef de Cuisine - Restaurants

Company: Eataly North America

Location: Chicago, IL

Posted Jun 23, 2025

Informs front of house personnel of menu changes, specials and shortages. Documents, investigates, escalates and resolves employee or guest incidents.

View Details Apply on SimplyHired

Client Service Representative I

Company: Canon U.S.A., Inc.

Location: Chicago, IL

Posted Jun 21, 2025

Responsible for performing general front office reception duties such as greeting visitors, answering phone calls, taking messages, scheduling conference rooms,…

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Staff Accountant

Company: StorSafe Self Storage

Location: Skokie, IL

Posted Jun 23, 2025

Loan entry and reconciliations- ensuring loan accuracy on a monthly basis. High School Graduate required; bachelor’s degree preferred. AP and AR as needed.

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full time academic

Assistant Professor of Urology

Company: UIC

Location: Chicago, Illinois

Posted Jun 22, 2025

View Details Apply on healthecareers.com

Kitchen Operations Supervisor

Company: CookUnity

Location: Chicago, IL

Posted Jun 23, 2025

Culinary degree or certification from a recognized culinary institution is desirable. Implement strategies to reduce food waste and enhance overall kitchen…

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full time

Clinical Associates in Gynecologic Oncology

Company: The University of Chicago

Location: Chicago, Illinois

Posted Jun 23, 2025

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full time be or bc academic

Critical Care Medicine/Generalist Anesthesiology Faculty Position

Company: Loyola Medicine

Location: Chicago, Illinois

Posted Jun 22, 2025

View Details Apply on healthecareers.com

Registered Nurse Operations Coordinator Neurosurgery Full Time Days

Company: Northwestern Medicine

Location: Chicago, IL

Posted Jun 21, 2025

Current license as a Registered Professional Nurse or eligible in the State of Illinois. Supervise and direct the office’s front-line clinical and clerical…

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sign-on bonus relocation assistance loan repayment program

Obstetrics Gynecology

Company: Advocate Health

Location: Chicago, Illinois

Posted Jun 22, 2025

View Details Apply on healthecareers.com

District Sales Manager-Joint Care

Company: Fidia Pharma USA

Location: Chicago, IL

Posted Jun 23, 2025

Must hold a valid driver’s license and clean driving record. A bachelor’s degree in business, marketing, or a related field from an accredited college or…

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full time

Chief - Section of Maternal Fetal Medicine

Company: The University of Chicago

Location: Chicago, Illinois

Posted Jun 22, 2025

View Details Apply on healthecareers.com
full time

Endovascular Neurosurgeons

Company: The University of Chicago Medicine & Biological Sciences

Location: Chicago, Illinois

Posted Jun 22, 2025

View Details Apply on healthecareers.com

Frequently Asked Questions

What are typical salary ranges for PTO roles by seniority?
Entry‑level PTO Analyst salaries range from $55,000 to $70,000 annually, mid‑level analysts earn $70,000 to $90,000, and senior PTO Program Managers or HRIS specialists command $90,000 to $120,000 plus bonus potential.
What skills and certifications are required for PTO positions?
Core skills include proficiency with HRIS platforms (Workday, SAP SuccessFactors, BambooHR), data analysis in Excel or Power BI, and regulatory knowledge of FMLA, ADA, and state leave laws. Certifications such as Certified Compensation Professional (CCP), HR Certification Institute (HRCI) HR-CP, or Workday HCM Associate enhance credibility.
Can PTO roles work remotely?
Yes, many PTO analysts and program managers operate fully remote, especially in tech firms. Remote work is supported by cloud‑based HRIS, secure VPNs, and collaboration tools like Slack and Microsoft Teams. Some roles still require occasional on‑site visits for policy rollout.
What are common career progression paths in PTO?
A PTO analyst can advance to Senior PTO Analyst, then to PTO Program Manager, followed by Director of Employee Benefits or HR Director roles. Lateral moves into broader HR analytics or compensation strategy are also common.
What industry trends are shaping PTO work?
Trends include the adoption of unlimited PTO policies, AI‑driven leave prediction models, integration of PTO data with wellness initiatives, and increased regulatory scrutiny on equitable leave practices. Companies also use data analytics to demonstrate ROI on PTO policies.

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