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.

Maintenance Supervisor

Company: Servitas Management Group, LLC

Location: Chicago, IL

Posted May 27, 2025

During performance of duties, documents and reports items to Management requiring repair or any suspicious or unlawful items around the facility or students,…

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full time be or bc academic

Urologist - Andrology Infertility

Company: Loyola Medicine

Location: Chicago, Illinois

Posted May 26, 2025

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full time be or bc academic

Assistant/Associate/Full Professor of Otolaryngology-Head & Neck Surgery/Neurotologist

Company: University of Illinois Chicago

Location: Chicago, Illinois

Posted May 25, 2025

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full time academic be or bc

Northwestern Medicine-Endocrinology – Clinician Educator

Company: Northwestern University

Location: Chicago, Illinois

Posted May 25, 2025

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full time

Chief - Section of Maternal Fetal Medicine

Company: The University of Chicago

Location: Chicago, Illinois

Posted May 25, 2025

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Senior Project Manager - JOC Projects - Chicago

Company: Michael Page

Location: Chicago, IL

Posted May 28, 2025

Monitor project progress and make necessary adjustments to ensure successful project completion. Maintain accurate project documentation, including project…

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Security and Facilities Lead

Company: KITH

Location: Chicago, IL

Posted May 27, 2025

Handles undesired conduct, violations of building policy and civil laws as warranted for the security and safety of guests, employees, patrons, and property.

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Metal Stamping Press Operator/Die Setter

Company: Weiss-Aug – Elk Grove Village, IL

Location: Elk Grove Village, IL

Posted May 24, 2025

Inspect work pieces for conformance to specifications, using micrometer or other measuring instruments to verify workmanship standards.

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Project Manager

Company: Keller North America, Inc.

Location: Chicago, IL

Posted May 24, 2025

Assembles proposals which includes performing risk assessment, evaluating opportunities to increase profit, estimating, engineering, technical writing, site…

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dental insurance health insurance profit sharing

Illinois - Elevate Your Career as a Board-Certified Dermatologist with a Leading Private Practice in Chicago - Unmatched Career Potential!

Company: myDermRecruiter

Location: Chicago, Illinois

Posted May 25, 2025

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Security & Safety Officer - Evening Shift

Company: Loyola University Health System

Location: Berwyn, IL

Posted May 27, 2025

General - Valid Illinois driver's license. Specify Degree(s): Criminal Justice, Law Enforcement, Security Admin, Fire Services or related field.

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Machine Operator | 3rd Shift

Company: Verstela

Location: Northlake, IL

Posted May 24, 2025

Maintenance & Troubleshooting: Perform routine maintenance on equipment, troubleshoot issues, and assist in basic repairs to minimize downtime.

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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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