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.

Accountant, General Accounting - YESS Finance - National Office (Remote)

Company: YMCA

Location: Chicago, IL

Posted Sep 26, 2025

Minimum bachelor’s degree in accounting or finance. Prepare, code and record entries and transactions in the production of financial statements and reports.

Graphic Designer

Company: The School of The Art Institute of Chicago

Location: Chicago, IL

Posted Sep 25, 2025

News and World Report, SAIC provides an interdisciplinary approach to art and design as well as world-class resources, including the Art Institute of Chicago…

Benefits Client Services Representative I

Company: PAYLOCITY CORPORATION

Location: Schaumburg, IL

Posted Sep 25, 2025

The Benefit Account Manager I plays a pivotal role in resolving client payroll and HR system challenges while fostering exceptional customer relationships…

Nurse Surveyor (HEALTH FACILITIES SURVEILLANCE NURSE)

Company: State of Illinois

Location: Westchester, IL

Posted Sep 26, 2025

Requires appropriate, valid driver’s license. Requires (a) graduation from an approved nursing education program resulting in an associate or a diploma degree…

Director of Content Marketing (Remote Available)

Company: S&S Activewear LLC

Location: Bolingbrook, IL

Posted Sep 25, 2025

Define and own go-to-market messaging across all stages of the customer journey, ensuring consistency across web, email, events, sales enablement, catalogs, and…

Cyber - Enterprise Security - Microsoft M365 Security Senior Manager

Company: Deloitte

Location: Chicago, IL

Posted Sep 26, 2025

Lead teams documenting platform technical issues, analysis, client communication, and resolution as part of cyber risk mitigation steps.

Industrial Maintenance Electrician | $52+/hr | 1st Shift

Company: Helion Group

Location: Cicero, IL

Posted Sep 25, 2025

*8+ years* of experience in *industrial electrical maintenance*, preferably in a *manufacturing environment*. *Trace and diagnose* control and power circuits to…

Access Control Analyst

Company: HighTower Advisors

Location: Chicago, IL

Posted Sep 25, 2025

Associate’s degree in information technology or Cybersecurity, relevant certifications or related field preferred; or equivalent relevant experience.

Closet Installer

Company: Perfection Custom Closets

Location: Niles, IL

Posted Sep 25, 2025

*Valid driver’s license with clean MVR (Required)*. Read and follow design plans, layouts, and measurements. Ability to safely use hand and power tools.

Commercial/Residential HVAC Service Technician

Company: Air-Rite Heating & Cooling, Inc

Location: Chicago, IL

Posted Sep 25, 2025

This position requires the ability to work independently in the field, manage service calls efficiently, and maintain clear communication with clients and…

Healthcare Data Analyst

Company: The University of Chicago

Location: Chicago, IL

Posted Sep 25, 2025

Master’s degree in biostatistics, computer science, or other related field OR requisite job experience in statistical analysis. Expert in SQL and Excel.

CNC / Swiss Machine Operator (2nd / 3rd shift)

Company: Viant Medical

Location: Wheeling, IL

Posted Sep 26, 2025

Viant provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual…

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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