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: Center Home for Hispanic Elderly

Location: Chicago, IL

Posted Aug 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…

CDL A Tanker Driver - Up to $1800 / wk

Company: Bulk Transport Company Inc

Location: Chicago, IL

Posted Aug 14, 2025

$1,500 driver referral bonus. 2+ years tractor-trailer experience _OR _. 6+ months liquid tanker experience. Utilization bonus: earn up to an additional 3 CPM\*…

Registered Nurse, Plastic Surgery Clinic

Company: Loyola University Health System

Location: Oakbrook Terrace, IL

Posted Aug 14, 2025

Certification reimbursement (up to 1 certification). Develops and implements individualized care plans based on these assessments.

Sales Engineer (Healthcare)

Company: Gong.io Inc.

Location: Chicago, IL

Posted Aug 13, 2025

Customer facing experience in a sales engineering role (pre-sales) or a combination of sales engineering and other relevant work experience (ie: Sales…

Commercial Roofing Field Supervisor- Villa Park, IL

Company: NATIONS ROOF LLC

Location: Villa Park, IL

Posted Aug 14, 2025

Requires a valid driver’s license and insurable driving record. Oversee field staff and/or sub-contractor(s), assisting with crew leadership, as required.

Welder

Company: PGNA INC

Location: Niles, IL

Posted Aug 14, 2025

The Group is close to its customers, on a global basis, through continuous technical assistance and support from the design phase to the installation and start-…

Graphic Designer

Company: FISHER PRINTING

Location: Bridgeview, IL

Posted Aug 13, 2025

Candidate will work with our database to locate and import graphic and text files. Fisher Printing designs ads and signage for retailers nationwide that are…

Manager, Full-Stack Software Engineer - Fintech & Tax Domain

Company: Deloitte

Location: Chicago, IL

Posted Aug 14, 2025

A bachelor's degree in computer science, software engineering, or a related discipline. Prior software engineering experience with the understanding of Business…

Welder

Company: Piovan

Location: Niles, IL

Posted Aug 14, 2025

The Group is close to its customers, on a global basis, through continuous technical assistance and support from the design phase to the installation and start-…

Bilingual Customer Service (Haitian Creole/English) – Call Center

Company: American Freedom Insurance Company

Location: Mount Prospect, IL

Posted Aug 13, 2025

*Career Development:* Paid training, ergonomic workstations, and state licensing reimbursement, professional development with advancement opportunities.

CNC Machine Operators-All Levels

Company: Strange Engineering

Location: Morton Grove, IL

Posted Aug 14, 2025

Familiar and able to read blueprints and use measuring instruments. Operate multiple machines when needed. Experience with Mazak or Okuma machines preferred.

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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