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.

Maintenance Electrician - Bridgeview, IL

Company: Signode

Location: Bridgeview, IL

Posted May 30, 2025

Provide electrical support for all production lines and will be responsible for installing and programming electrical equipment.

CDL-A Regional Tanker Truck Driver

Company: TransWood

Location: Chicago, IL

Posted May 31, 2025

Good driving record with no major violations or accidents (some restrictions apply). 401(k) with employer matching. Hauling liquid chemicals in a liquid tanker.

Retail Sales and Store Support

Company: Jewel Osco

Location: Chicago, IL

Posted Jun 01, 2025

Health and welfare benefits for eligible employees (Medical, Dental, 401k and more!).

Class A Regional Driver- Champaign, IL

Company: Whiteline Express Ltd

Location: Chicago, IL

Posted May 31, 2025

Must meet DOT driving standards. Up to $0.12 per mile for driver referral program. Minimum of 6 months of Class A tractor/trailer experience within the past 24…

Temp Services Care Agent

Company: Lakeshore Recycling Systems LLC

Location: Rosemont, IL

Posted Jun 02, 2025

Take incoming sales calls to determine customer needs, provide proposals and close sales. Manage incoming internet leads through Salesforce and follow-up with…

2026 Commercial & Investment Bank Innovation Development Summer Analyst Program

Company: JPMorganChase

Location: Chicago, IL

Posted May 31, 2025

Problem-solving skills in interpreting data, trends, and insights to identify opportunities and develop actionable solutions. Analyze data to drive decisions.

Class A Regional Driver- Jackson Ctr, OH

Company: Whiteline Express Ltd

Location: Chicago, IL

Posted May 31, 2025

Must meet DOT driving standards. Up to $0.12 per mile for driver referral program. Minimum of 6 months of Class A tractor/trailer experience within the past 24…

Marketing Manager

Company: MillerKnoll

Location: Chicago, IL

Posted Jun 02, 2025

5–7 years in marketing or agency roles (advertising, PR, or integrated marketing); luxury, fashion, or design-focused brand experience preferred, with B2B or…

Plumber or Plumber Apprentice

Company: J Mac Mechanical

Location: Chicago Ridge, IL

Posted Jun 02, 2025

Must have own hand tools and a form of transportation to get to work. Must be able to listen to instruction and both work with others and by yourself.

Security Analyst

Company: Blume Global

Location: Chicago, IL

Posted May 31, 2025

Able to communicate effectively in verbal and written format with technical and non-technical audiences. Relevant certification such as CISSP, CCNA, CompTIA…

CDL-A Independent Contractor Truck Driver

Company: TransAm Trucking

Location: Chicago, IL

Posted Jun 01, 2025

Must have at-least 12 months of verified tractor-trailer driving experience. No reckless driving violations in the last 5 years.

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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