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.

Transporation Security Officer

Company: Department of Homeland Security - Transportation Security Administration

Location: Peoria, IL

Posted Jul 14, 2025

View Details Apply on usajobs.gov

Customer Service Representative

Company: Lawson Products

Location: Chicago, IL

Posted Jul 14, 2025

Responds to a minimum of 40 calls per day in an inbound call center. Possesses entry-level problem solving kills. High School Diploma or GED.

View Details Apply on SimplyHired

Unarmed Security Officer #247

Company: Stark Security Inc

Location: Chicago, IL

Posted Jul 14, 2025

Make guests aware of rules that must be adhered to. Occasional – reaching, stooping, climbing, balancing, driving, bending, twisting, handling paperwork.

View Details Apply on SimplyHired

Physician (Staff Pathologist)

Company: Department of Veterans Affairs - Veterans Health Administration

Location: Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on usajobs.gov

Housekeeping Aid Supervisor

Company: Department of Veterans Affairs - Veterans Health Administration

Location: North Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on usajobs.gov

Senior Accountant/Bookkeeper

Company: STANLEY ZILBER & ASSOCIATES, PC

Location: Chicago, IL

Posted Jul 14, 2025

We are seeking a detail-oriented and experienced Senior Accountant/Bookkeeper. The ideal candidate will possess a strong background in Construction Accounting…

View Details Apply on SimplyHired

Psychiatrist

Company: Department of Veterans Affairs - Veterans Health Administration

Location: North Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on usajobs.gov

Copywriter HYBRID — FULL-TIMECHICAGO

Company: Edelman

Location: Chicago, IL

Posted Jul 14, 2025

High-level concepting, tactical program ideation and copywriting for a wide range of brand experiences, social content and marketing deliverables that generate…

View Details Apply on SimplyHired
full time research academic

Assistant/Associate/Full Professor of Otolaryngology-Head & Neck Surgery/Neurotologist

Company: University of Illinois Chicago

Location: Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on healthecareers.com

Registered Nurse- FT/PT PM Shift Only!

Company: Pearl of Montclare

Location: Elmwood Park, IL

Posted Jul 14, 2025

Prepare & administer medications as ordered by the physician. Admit, transfer and discharge residents as required. Join The Pearl of Montclare!

View Details Apply on SimplyHired
relocation assistance full time be or bc

Gastroenterologist Opportunity – Established Group in Chicago

Company: RosmanSearch

Location: Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on healthecareers.com

Associate Manager, Investment, Search

Company: Rise

Location: Chicago, IL

Posted Jul 14, 2025

Collaborate with leadership and peers to develop solutions that will enhance our operational efficiency, tools, and systems, and improve current workflows.

View Details Apply on SimplyHired

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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