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.

CAD Program Manager

Company: The Container Store Inc.

Location: Elmhurst, IL

Posted Jul 12, 2025

Bachelor's degree in Engineering, Computer Science, or related field. 4-7 years of experience in CAD program management or related field.

View Details Apply on SimplyHired

Preschool Assistant Director River North

Company: Kido

Location: Chicago, IL

Posted Jul 12, 2025

Oversee curriculum implementation and ensure licensing compliance. CDA or Bachelor’s degree in Early Childhood or a related field.

View Details Apply on SimplyHired

Insurance Sales Agent - Customer Service

Company: Freeway Insurance Services America, LLC

Location: Berwyn, IL

Posted Jul 12, 2025

Personal Lines or Property and Casualty license preferred (but not required). Accurate accounting of all currency transactions as well as timely delivery of…

View Details Apply on SimplyHired

Police Officer

Company: Department of Veterans Affairs - Veterans Health Administration

Location: North Chicago, Illinois

Posted Jul 13, 2025

View Details Apply on usajobs.gov

Public Safety Supervisor (Armed) 3rd Shift

Company: Advocate Aurora Health

Location: Chicago, IL

Posted Jul 12, 2025

A valid driver’s license issued by the Division of Motor Vehicle. Responsible for KRA results; provides input to and implements the budget, administers policies…

View Details Apply on SimplyHired

Flex Security Officer - Open Schedule

Company: Securitas

Location: McCook, IL

Posted Jul 12, 2025

Provide high level of customer service to clients, employees, and guests. Valid Driver's License and clear driving history. Prior security experience a plus.

View Details Apply on SimplyHired

Senior Brand Manager, Brand Growth & Innovation - Cottonelle®

Company: Kimberly-Clark

Location: Chicago, IL

Posted Jul 13, 2025

Lead portfolio technology mapping and cascade strategy, including business case ownership of big technical bets. Bachelors Degree in Business/Marketing.

View Details Apply on SimplyHired

Insurance Sales Agent - Customer Service

Company: Freeway Insurance Services America, LLC

Location: Addison, IL

Posted Jul 12, 2025

Personal Lines or Property and Casualty license preferred (but not required). Accurate accounting of all currency transactions as well as timely delivery of…

View Details Apply on SimplyHired
loan repayment program malpractice insurance relocation assistance

Endocrinologist in Peoria, Illinois

Company: OSF Medical Group Provider Recruitment

Location: Peoria and Galesburg, IL

Posted Jul 13, 2025

View Details Apply on healthecareers.com

CNC Machinist- Set Up/Operator

Company: AppleOne

Location: Alsip, IL

Posted Jul 12, 2025

Load tools, molds, and rollers into machines according to specifications. Strong mechanical aptitude with solid troubleshooting ability.

View Details Apply on SimplyHired

Welder 1/Fabrication

Company: Weiss-Aug – Elk Grove Village, IL

Location: Elk Grove Village, IL

Posted Jul 12, 2025

Minimum of 1 year of manufacturing experience. Give finished tank an inspection to ensure tank meets customer visual requirements, i.e. weld spatter removed,…

View Details Apply on SimplyHired

Executive Sous Chef | Full-Time | McCormick Place Convention Center

Company: Oak View Group

Location: Chicago, IL

Posted Jul 13, 2025

Continually manage, monitor and seek labor efficiencies to reduce costs, improve product output and enhance overall guest experience.

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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