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.

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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ERP Project Manager – PLEX

Company: Weiss-Aug – Elk Grove Village, IL

Location: Elk Grove Village, IL

Posted May 28, 2025

A bachelor’s degree in an information systems field, such as CIS, BIS or MIS degree and 5-10 years’ experience as a business analyst, software developer or…

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Pharmacist Centralized Services Work From Home - NY

Company: WALGREENS

Location: Deerfield, IL

Posted May 28, 2025

Current Pharmacist license as granted by the appropriate state licensing authority. Willing to travel up to 10% of the time for business purposes (within state…

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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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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 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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