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.

Retail Sales Associate / Design Associate (Home Furnishings)

Company: Room & Board

Location: Chicago, IL

Posted Aug 14, 2025

2+ years of experience working in a customer-centric, fashion/design savvy retail environment with a passion for design and engaging with customers on the…

View Details Apply on SimplyHired
dental insurance health insurance relocation assistance

Clinical Associates - Developmental and Behavioral Pediatrics

Company: The University of Chicago

Location: Chicago, Illinois

Posted Aug 14, 2025

View Details Apply on healthecareers.com

Ambulatory RN 2 - OB-GYN - Part-time with Benefits!

Company: Rush University Medical Center

Location: Chicago, IL

Posted Aug 14, 2025

Current license and credentials by the state they are assigned. 6.Utilizes evidence-based ambulatory care nursing interventions during clinical visits,…

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CDL A Tanker Driver - Up to $1800 / wk

Company: Bulk Transport Company Inc

Location: Chicago, IL

Posted Aug 14, 2025

$1,500 driver referral bonus. 2+ years tractor-trailer experience _OR _. 6+ months liquid tanker experience. Utilization bonus: earn up to an additional 3 CPM\*…

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Registered Nurse, Plastic Surgery Clinic

Company: Loyola University Health System

Location: Oakbrook Terrace, IL

Posted Aug 14, 2025

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

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Commercial Roofing Field Supervisor- Villa Park, IL

Company: NATIONS ROOF LLC

Location: Villa Park, IL

Posted Aug 14, 2025

Requires a valid driver’s license and insurable driving record. Oversee field staff and/or sub-contractor(s), assisting with crew leadership, as required.

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Welder

Company: PGNA INC

Location: Niles, IL

Posted Aug 14, 2025

The Group is close to its customers, on a global basis, through continuous technical assistance and support from the design phase to the installation and start-…

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Sr. InfoSec Governance Analyst - Hybrid

Company: Alliant Credit Union

Location: Chicago, IL

Posted Aug 14, 2025

Associate Degree - Information Security or Related field - Minimum. Ensures compliance with all applicable state and federal laws, company procedures and…

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CDL A OTR Truck Driver - Up to $110,000 / yr

Company: American Central Transportation

Location: Chicago, IL

Posted Aug 14, 2025

$1,500 driver referral bonus. HIGH STANDARDS=HIGH PAY: *Average driver earns $90K; up to $110K per year*. *Choose your home time: drivers are home 7 days per…

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Welder

Company: Piovan

Location: Niles, IL

Posted Aug 14, 2025

The Group is close to its customers, on a global basis, through continuous technical assistance and support from the design phase to the installation and start-…

View Details Apply on SimplyHired

Public Safety Officer I - Armed (On-Call, 1st Shift)

Company: Advocate Aurora Health

Location: Park Ridge, IL

Posted Aug 14, 2025

A valid driver’s license issued by the Division of Motor Vehicle. Responds to service calls, such as combative or threatening patients or visitors and team…

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Practice Architect, AI, Google Cloud

Company: Google

Location: Chicago, IL

Posted Aug 14, 2025

You will orchestrate across numerous contributing teams including solutions, services, partners, product engineering, marketing, and GTM stakeholder…

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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