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.

C# Engineer

Company: BlackRock Investments

Location: Chicago, IL

Posted Aug 06, 2025

Participate in cross-functional feature requirements gathering, design, and implementation. You will collaborate with experienced engineers to develop and…

CDL-A Truck Driver - 1099 - Up to $5,000 / week

Company: P&S

Location: Chicago, IL

Posted Aug 06, 2025

Truck payment: $500/week to $650/week depending on truck. No credit check, $0 down. Balloon payment at end of term. Earn 70% of line haul.

Global Practice Architect, Infrastructure III, Google Cloud

Company: Google

Location: Chicago, IL

Posted Aug 06, 2025

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

Pre-Certification & Call Center Representative

Company: VitalSkin Dermatology

Location: Chicago, IL

Posted Aug 06, 2025

You are able to perform all aspects of a call center: manage a high volume of incoming calls in a small, centralized call center; obtain information from the…

Python Developer

Company: BlackRock Investments

Location: Chicago, IL

Posted Aug 06, 2025

Participate in cross-functional feature requirements gathering, design, and implementation. You will collaborate with experienced engineers to develop and…

Data Scientist II, Condition Monitoring

Company: Caterpillar

Location: Chicago, IL

Posted Aug 06, 2025

In-depth technical and problem-solving skills and evidence of continuous learning in the analytics field. Programming Languages: Working knowledge of basic…

Project Manager II

Company: Gilbane Building Company

Location: Chicago, IL

Posted Aug 06, 2025

Participates in enrollment for insurance and bonds; tracks and obtains trade contractors’ compliance. Strong technical and communication skills are critical.

Dump Truck Driver

Company: Hana Transport Inc.

Location: Chicago, IL

Posted Aug 06, 2025

Valid commercial driver's license (CDL A) with, 3+ years experience in dump/must have a clean CDL License with no more than 2 tickets in the past 3-years.

Tool Room Machinist 1st shift)

Company: Klein Tools

Location: Elk Grove Village, IL

Posted Aug 06, 2025

Fits and assembles parts into complete assembly, using jigs, fixtures, surface plates, surface table, hand tools and power tools. Ability to weld is a plus.

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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