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.

Lead Software Engineer, Full stack

Company: Capital One

Location: Chicago, IL

Posted Aug 25, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

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dental insurance health insurance health savings account

Nurse Practitioner - APRN - Palliative Care

Company: Endeavor Health

Location: Naperville, Elmhurst, Plainfield, IL

Posted Aug 24, 2025

View Details Apply on healthecareers.com

Seasonal Sales Associate

Company: Nespresso

Location: Chicago, IL

Posted Aug 25, 2025

As the welcoming face of our retail boutique, you will greet customers, offer complimentary coffee tastings, help with boutique operations and provide an…

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TIG Welder/Fabricator

Company: Meyer Tool & Mfg., Inc.

Location: Oak Lawn, IL

Posted Aug 24, 2025

Paid on-the-job ASME Pressure Vessel Code weld training and certification. Inspect your own welds, identify defects or issues, and make corrections.

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Retail Sales Associate

Company: Windy City Diamonds

Location: Chicago, IL

Posted Aug 24, 2025

This individual will be the face of our brand, delivering exceptional customer experiences and driving revenue growth through expert product knowledge,…

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Class A Commercial Driver

Company: CarMax

Location: Chicago, IL

Posted Aug 25, 2025

Valid state-issued commercial driver’s license Class A (CDL) Required. Except as otherwise required by state law, CarMax Associates are entitled to the…

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Nurse Associate - Dermatology & Neurosciences, Full-Time, Days

Company: UChicago Medicine

Location: Chicago, IL

Posted Aug 25, 2025

Must be an actively licensed Registered Nurse in the state of Illinois. Conducts, responds to, follow up on, and triages patient phone calls to the physician as…

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Registered Nurse/Ultrasound Tech

Company: Women's Care Center

Location: Chicago, IL

Posted Aug 25, 2025

Our mission is simple: to help pregnant women from our communities choose life for their babies, have healthier pregnancies, become better parents and take…

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Sous Chef

Company: Bazaar Meat by Jose Andres

Location: Chicago, IL

Posted Aug 25, 2025

Train and develop kitchen staff; train cooks/kitchen staff in the importance of consistency in preparation and presentation.

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CDL-A Company Driver

Company: Dollar General

Location: Chicago, IL

Posted Aug 25, 2025

1+ years CDL A driving experience. Must be 21 years of age. Experience preferred, requirement based on location. Short term and long term disability.

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health system full-time

Advanced Practice Registered Nurse (APRN) - Cardiology - Medical Group

Company: Endeavor Health

Location: Chicago, Illinois

Posted Aug 24, 2025

View Details Apply on healthecareers.com

HVAC Service Technician/ Installer

Company: Precision Heating and Cooling

Location: Alsip, IL

Posted Aug 25, 2025

Come and join the area's premier Heating and Air Conditioning contractor. We offer year round work as well as a complete and excellent benefits package.

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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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