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.

Client Service Representative

Company: Viking Gymnastics

Location: Niles, IL

Posted Mar 26, 2025

Our reception staff must consistently greet clients, answer telephones, offer assistance, use professional verbiage, and always make themselves available to the…

View Details Apply on SimplyHired

Generative AI Engineer

Company: CME Group

Location: Chicago, IL

Posted Mar 26, 2025

Software Engineering Excellence: Deep understanding of software engineering best practices, including code quality, testing, low-level design, software design…

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Property Accountant

Company: ENCORE SENIOR LIVING

Location: Chicago, IL

Posted Mar 28, 2025

The successful candidate has a bachelors degree in accounting - minimum 3- 5 years full cycle accounting experience.

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sign-on bonus part time

Home Health SLP, Part Time $10,000 Bonus

Company: Residential Home Health and Hospice

Location: CHICAGO, Illinois

Posted Mar 26, 2025

View Details Apply on healthecareers.com
full time

OBGYN Physician

Company: No Employer

Location: Chicago, Illinois

Posted Mar 30, 2025

View Details Apply on healthecareers.com

Experienced Carpenter/tradesman

Company: Davies Home Services

Location: Park Ridge, IL

Posted Mar 29, 2025

Strong skills in restoration techniques, framing, construction, painting, siding installation, tile laying, drywall.

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Sous Chef

Company: LSG Sky Chefs

Location: Des Plaines, IL

Posted Mar 28, 2025

Understand and demonstrate concepts of financial controls (ex: keep food cost within budget, control stock levels while being cost conscious, minimize waste).

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dental insurance health insurance life insurance

Registered Vascular Technologist

Company: Cook County Health

Location: Chicago, Illinois

Posted Mar 26, 2025

View Details Apply on healthecareers.com
health system full time

Physician Assistant - Wound Care Center- Swedish Hospital

Company: Endeavor Health

Location: Chicago, Illinois

Posted Mar 30, 2025

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health system full time be or bc

Emergency Medicine Radiologist - Remote or Hospital Based

Company: Endeavor Health

Location: Evanston and Glenview, IL

Posted Mar 31, 2025

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full time academic be or bc

Urologist

Company: Loyola Medicine

Location: Chicago, Illinois

Posted Mar 26, 2025

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full time be or bc academic

Pulmonary and Critical Care Medicine: Interventional Pulmonary Clinician-Educator

Company: Northwestern University

Location: Chicago, Illinois

Posted Mar 26, 2025

View Details Apply on healthecareers.com

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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