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.

UI/UX Designer

Company: Velvetech

Location: Chicago, IL

Posted Feb 22, 2025

Proficiency in AI-driven design tools such as Figma with AI plugins, Adobe XD with Sensei features, or similar is required.

View Details Apply on SimplyHired

Backend Software Engineer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Feb 21, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

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Pharmacist-Drug Diversion Surveillance Analyst, Full-time Days

Company: Northwestern Medicine

Location: Chicago, IL

Posted Feb 20, 2025

We consider this on a case-by-case basis and follow all state and federal guidelines. We offer a wide range of benefits that provide employees with tools and…

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hospital travel

Travel Registered Respiratory Therapist - $2,065 per week

Company: Ann & Robert H. Lurie Childrens Hospital of Chicago

Location: Chicago, Illinois

Posted Feb 18, 2025

View Details Apply on healthecareers.com

AI Training Physics - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Feb 21, 2025

You can work on your own schedule. You will measure the progress of these AI chatbots, evaluate their logic, and solve problems to improve the quality of each…

View Details Apply on SimplyHired

Senior Data Analyst

Company: Chicago Public Schools

Location: Chicago, IL

Posted Feb 24, 2025

Effectively communicate technical findings to both technical and non-technical audiences. Strong understanding of statistical concepts and data analysis…

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contract travel health insurance

Travel Nurse RN - Bone Marrow Transplant - $2,494 per week

Company: Stability Healthcare

Location: Chicago, Illinois

Posted Feb 19, 2025

View Details Apply on healthecareers.com

Senior Director, Insurance Institutional Sales

Company: The Federal Home Loan Bank of Chicago

Location: Chicago, IL

Posted Feb 18, 2025

Drive Business Growth: By developing and executing strategic account plans, you’ll directly contribute to meeting sales objectives and driving significant…

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Registered Nurse, Family Practice

Company: Loyola University Health System

Location: Berwyn, IL

Posted Feb 20, 2025

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

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prn retirement plan tuition reimbursement

Home Health Occupational Therapist - $94K+ per year

Company: LHC Group

Location: Chicago Heights, Illinois

Posted Feb 19, 2025

View Details Apply on healthecareers.com

Registered Nurse

Company: DAVITA

Location: Chicago, IL

Posted Feb 19, 2025

Comprehensive benefits: medical, dental, vision, 401k, paid time off, PTO cash out, DaVita-negotiated discounts on hundreds of items from your cell phone plan…

View Details Apply on SimplyHired

Plumbing Service Technician

Company: Stellar Plumbing

Location: Elk Grove Village, IL

Posted Feb 24, 2025

Plumbing Service Technicians determine service needs, quote prices in the field and perform repairs. Must be willing to pursue, develop, and participate in…

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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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