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.

Lead Electrician

Company: Dart Container

Location: Chicago, IL

Posted Jul 18, 2025

Maintain, install, and repair equipment, electrical and electronic systems and facility electrical systems. Plan layout of wiring and install conduit, wiring…

Machine Operator (Experienced) needed for a Paper Laminating, Coating & Converting Co--Day Shift

Company: Midwest Laminating

Location: Alsip, IL

Posted Jul 18, 2025

Accurately measure and cut paper using tape measures and other tools. Strong mechanical aptitude and problem-solving skills. Paid vacation time and holiday pay.

Thermoforming - Process Technician

Company: Pactiv Evergreen

Location: Bridgeview, IL

Posted Jul 18, 2025

Two or four year technical degree or certification. Partner with plant Training Coordinator to develop and conduct training programs for line operators and…

Commercial HVAC Service Manager

Company: Bedco Mechanical

Location: Chicago, IL

Posted Jul 18, 2025

This role is ideal for a field-experienced technician ready to step into a leadership role—or a current service manager who still enjoys rolling up their…

Public Health Nurse - Addison

Company: DuPage County Health Department

Location: Addison, IL

Posted Jul 18, 2025

Perform screenings (perinatal depression, social determinants of health, ages and stages). Registered Nurse (RN) licensed in the State of Illinois.

Commercial HVAC Service Technician

Company: Bedco Mechanical

Location: Chicago, IL

Posted Jul 18, 2025

This is a role for seasoned professionals who can take ownership of diagnosing and resolving complex mechanical issues in the field with minimal supervision.

Accounts Payable Accountant

Company: The Chicago Housing Authority

Location: Chicago, IL

Posted Jul 18, 2025

Must possess a bachelor’s degree in Accounting, Finance or Business Administration or a related business field and at least two (2) years of accounting…

Project Accountant

Company: Expansive

Location: Chicago, IL

Posted Jul 18, 2025

This position is intended as an entry-level position with potential for growth into a Property Accountant.  Approve and process invoices for payment.

Sales Associate - Central Region

Company: Benjamin Moore & Co

Location: Chicago, IL

Posted Jul 18, 2025

Valid driver's license and a good driving record. Manage temporarily assigned territory, including scheduling, territory organization, and managing CRM/…

CNC Machinist/ Manufacturing / Production / Apprentice

Company: SCOT FORGE

Location: Franklin Park, IL

Posted Jul 18, 2025

Set up equipment, install tools and fixtures. At Scot Forge, we help our customers with forged solutions from the world's physical infrastructure, energy, and…

Local CDL A Truck Driver Hazmat

Company: Savage

Location: Chicago, IL

Posted Jul 18, 2025

Valid CDL with tanker and hazmat endorsements. Valid CDL with tanker and hazmat endorsements. The primary responsibility of the Sulphur Driver is to perform and…

PROJECT MANAGER - AFFORDABLE HOUSING

Company: Full Circle Communities

Location: Chicago, IL

Posted Jul 18, 2025

5 years of experience in the affordable housing field, 3 of which must be direct experience in affordable housing development. Close-out and Hand-off.

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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