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.

RN REGISTERED NURSES

Company: Park View

Location: Chicago, IL

Posted Jul 14, 2025

Current, unencumbered state license to practice as a Registered Nurse. Will direct the day-to-day functions of the nursing assistants in accordance with current…

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Field Supervisor

Company: Department of Commerce - U.S. Census Bureau

Location: Bureau County, IL

Posted Jul 13, 2025

View Details Apply on usajobs.gov

Field Supervisor

Company: Department of Commerce - U.S. Census Bureau

Location: Cook County, IL

Posted Jul 13, 2025

View Details Apply on usajobs.gov

Door Host/Security Staff - Late Nights, Evenings

Company: Gus' Sip & Dip (1262)

Location: Chicago, IL

Posted Jul 13, 2025

Door Host/Security Staff are responsible for the initial, warm greeting of guests and for maintaining the safety of guests and employees, carding guests,…

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RN REGISTERED NURSES

Company: Center Home for Hispanic Elderly

Location: Chicago, IL

Posted Jul 14, 2025

Current, unencumbered state license to practice as a Registered Nurse. Will direct the day-to-day functions of the nursing assistants in accordance with current…

View Details Apply on SimplyHired

Field Representative

Company: Department of Commerce - U.S. Census Bureau

Location: Kendall County, IL

Posted Jul 13, 2025

View Details Apply on usajobs.gov

Supervisory Information Technology Specialist (Policy and Planning)

Company: Department of the Army - U.S. Military Entrance Processing Command

Location: North Chicago, Illinois

Posted Jul 13, 2025

View Details Apply on usajobs.gov

Field Representative

Company: Department of Commerce - U.S. Census Bureau

Location: Kendall County, IL

Posted Jul 13, 2025

View Details Apply on usajobs.gov

Field Supervisor

Company: Department of Commerce - U.S. Census Bureau

Location: Kendall County, IL

Posted Jul 13, 2025

View Details Apply on usajobs.gov
relocation assistance full time be or bc

Gastroenterologist Opportunity – Established Group in Chicago

Company: RosmanSearch

Location: Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on healthecareers.com

Field Representative

Company: Department of Commerce - U.S. Census Bureau

Location: Cook County, IL

Posted Jul 13, 2025

View Details Apply on usajobs.gov

Field Supervisor

Company: Department of Commerce - U.S. Census Bureau

Location: Kendall County, IL

Posted Jul 13, 2025

View Details Apply on usajobs.gov

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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