Paid Time Off Jobs in Chicago, IL

72,501 open positions · Updated daily

Looking for Paid Time Off jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Paid Time Off position in the Chicago, IL area.

Maintenance Electrician (3rd Shift | $41.36/hr | Union | Direct Hire | Chicago, IL)

Company: Assist Staffing

Location: Chicago, IL

Posted Aug 17, 2025

Read and interpret electrical schematics and technical manuals. Minimum 3+ years’ experience in industrial maintenance with a strong electrical focus.

CNC Lathe Operator (2nd Shift)

Company: ERA Industries LLC

Location: Elk Grove Village, IL

Posted Aug 17, 2025

Ability to use basic measuring tools (Micrometer, Caliper, Thread Gages, Pin Gages, Bore Gages, Dial Indicators, Height Gages). Assist with machine set up.

On Call Hospice RN

Company: Oasis Hospice & Palliative Care, Inc.

Location: Chicago, IL

Posted Aug 18, 2025

Must be a licensed driver with an automobile that is insured in accordance with state of Illinois requirements and is in good working order.

Accounting Supervisor - Chicago IL, Loop

Company: Savant Wealth Management

Location: Chicago, IL

Posted Aug 18, 2025

*Lead with purpose:* Coach, develop, and empower a team of accountants, setting clear goals and aligning their efforts to Savant’s mission and strategic…

Class A CDL Owner Operator

Company: Trucking Edge

Location: Chicago, IL

Posted Aug 18, 2025

Earn 75% of line haul utilizing own trailer. 100% of billed fuel surcharge along with 100% of accessorials. Earn 70% of line haul revenue.

Private Equity Tech Sales - Founding Team Member for AI Startup

Company: Nestbox AI

Location: Chicago, IL

Posted Aug 18, 2025

*Founder-Level Impact:* You’ll be the first sales hire, working directly with our technical founders to shape GTM strategy, refine our offering for PE, and have…

Senior Manager - Global Payment Network Information Security Office (ISO) Consultant

Company: Capital One

Location: Chicago, IL

Posted Aug 18, 2025

Collaborating with enterprise cyber teams and tech architects in defining and driving the cyber architecture strategy and guiding principles for the…

Registered Nurse Hospice Case Manager - Flexible Schedule

Company: LifeChoice Hospice and Palliative Care

Location: Mount Prospect, IL

Posted Aug 18, 2025

Current RN license in IL. Perform and document patient evaluations, visits, and care in compliance with federal, state, and accreditation standards.

Unarmed Security Officer ( North/West Suburbs)

Company: American Public Defense Inc.

Location: Chicago, IL

Posted Aug 17, 2025

Valid driver's license/state ID. Logging in vendors and visitors. Maintain safety and security of property. Complete daily logs and incident reports.

Senior Manager - Global Payment Network Information Security Office (ISO) Consultant

Company: Capital One

Location: Chicago, IL

Posted Aug 18, 2025

Collaborating with enterprise cyber teams and tech architects in defining and driving the cyber architecture strategy and guiding principles for the…

Customer Experience Supervisor

Company: TJ Maxx

Location: Oak Brook, IL

Posted Aug 17, 2025

Benefits include: Associate discount; EAP; smoking cessation; bereavement; 401(k) Associate contributions; child care & cell phone discounts; pet & legal…

Frequently Asked Questions

What are typical salary ranges for PTO roles by seniority?
Entry‑level PTO Analyst salaries range from $55,000 to $70,000 annually, mid‑level analysts earn $70,000 to $90,000, and senior PTO Program Managers or HRIS specialists command $90,000 to $120,000 plus bonus potential.
What skills and certifications are required for PTO positions?
Core skills include proficiency with HRIS platforms (Workday, SAP SuccessFactors, BambooHR), data analysis in Excel or Power BI, and regulatory knowledge of FMLA, ADA, and state leave laws. Certifications such as Certified Compensation Professional (CCP), HR Certification Institute (HRCI) HR-CP, or Workday HCM Associate enhance credibility.
Can PTO roles work remotely?
Yes, many PTO analysts and program managers operate fully remote, especially in tech firms. Remote work is supported by cloud‑based HRIS, secure VPNs, and collaboration tools like Slack and Microsoft Teams. Some roles still require occasional on‑site visits for policy rollout.
What are common career progression paths in PTO?
A PTO analyst can advance to Senior PTO Analyst, then to PTO Program Manager, followed by Director of Employee Benefits or HR Director roles. Lateral moves into broader HR analytics or compensation strategy are also common.
What industry trends are shaping PTO work?
Trends include the adoption of unlimited PTO policies, AI‑driven leave prediction models, integration of PTO data with wellness initiatives, and increased regulatory scrutiny on equitable leave practices. Companies also use data analytics to demonstrate ROI on PTO policies.

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