Generous Paid Time Off Jobs in Chicago, IL

73,229 open positions · Updated daily

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

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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

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Lamination Machine Operator - 2nd Shift w/ shift differential $$$

Company: PAXXUS

Location: Addison, IL

Posted Jun 23, 2025

Experience operating lamination equipment in a manufacturing facility. Ability to read user manuals and complete documentation in English.

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Carpenter / Home Improvement Specialist

Company: Mr. Handyman

Location: Chicago Ridge, IL

Posted Jun 23, 2025

Own your own professional grade tools for a large variety of jobs. The pay range for this position is $32 to $36+/hr and is dependent on your experience as a…

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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

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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 the typical salary ranges for Generous PTO roles by seniority?
Entry‑Level PTO Analyst: $55k–$70k; Mid‑Level PTO Manager: $80k–$110k; Senior PTO Director: $130k–$170k. These ranges vary by region and company size.
Which skills and certifications are required for Generous PTO positions?
Core skills: PTO policy design, HRIS configuration (Workday, SAP SuccessFactors), data analytics (SQL, Excel, Power BI), compliance knowledge (FERPA, GDPR). Certifications: SHRM‑CP/SHRM‑SCP, HRIS Certified Professional, Workday HCM Certification, SAP SuccessFactors HCM Certification.
Is remote work available for Generous PTO roles?
Approximately 70% of PTO analyst and benefits coordinator positions allow full‑time remote or hybrid work, especially in SaaS and tech firms. On‑site roles exist for compliance audit positions that require physical access to employee records.
What are the career progression paths in Generous PTO roles?
PTO Analyst → PTO Manager → PTO Director → HR Director / VP of People Experience → Chief People Officer. Each step expands strategic influence from policy design to workforce planning.
What are the current industry trends for Generous PTO?
AI‑driven leave analytics, continuous PTO policies, integration of mental‑health metrics, global time‑zone‑aware accrual systems, emphasis on employee well‑being dashboards. Companies are adopting flexible PTO models to attract and retain talent.

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