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.

General Construction Worker/Project Manager

Company: Archetype Homes, Inc

Location: Chicago, IL

Posted Aug 17, 2025

Complete carpentry tasks as directed, including rough framing, finish carpentry (trim), door hanging, window installation, deck building, cabinet installation,…

View Details Apply on SimplyHired

INSURANCE SALES AGENT-TEAM MEMBER

Company: STATE FARM INSURANCE

Location: Chicago, IL

Posted Aug 17, 2025

Answer calls from insurance customers promptly and provide a high level of service. Network in various ways to develop new prospects.

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dental insurance health insurance health savings account

Physician Assistant - PA - Palliative Care

Company: Endeavor Health

Location: Naperville, Elmhurst, Plainfield, IL

Posted Aug 17, 2025

View Details Apply on healthecareers.com

Housekeeping / Janitor Supervisor – Part-Time Hourly

Company: Villa Dubois Guest House

Location: Chicago, IL

Posted Aug 16, 2025

Clean guest rooms and common areas to a high standard. *Must have housekeeping/janitorial experience in hotels, Airbnb, or vacation rentals within the last 5…

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Truck Driver CDL A Daily

Company: Ryder

Location: Chicago, IL

Posted Aug 16, 2025

Ensuring compliance with applicable federal and/or state laws, regulations, and/or agency rules, standards and guidelines. Minimum 21 years of age.

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UNARMED Security Officer

Company: Gamma Team Security Inc

Location: Cicero, IL

Posted Aug 17, 2025

Valid registration as a security officer. Ability to operate surveillance equipment. Report on daily activities and any security incidents.

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Hospital Pharmacist Night Shift IL

Company: Soliant

Location: Evergreen Park, IL

Posted Aug 16, 2025

Doctor of Pharmacy (PharmD) degree, active Pharmacist license, and minimum 1+ years Pharmacist experience required.

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Cath Lab RN Travel Assignment in Chicago, IL

Company: Soliant

Location: Chicago, IL

Posted Aug 16, 2025

Bachelor of Science in Nursing (BSN) degree, active registered nurse (RN) license and minimum 1+ years RN experience required. Illinois RN license in hand.

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Executive Chef

Company: Catering by Michaels

Location: Morton Grove, IL

Posted Aug 16, 2025

Strong knowledge of financial management disciplines to include but not limited to P&L, budget design and management, and financial analysis.

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Janitor (Union) - Logan Square

Company: HHDC

Location: Chicago, IL

Posted Aug 16, 2025

Ability to work with lawn machinery and power tools. Keeps up the exterior cleanliness and presentation of the property, including lawn care, window washing (…

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Insurance Agent Customer Service Rep/Team Member

Company: State Farm Insurance Chicago,Illinois

Location: Chicago, IL

Posted Aug 17, 2025

Be able to discover gaps in insurance customers' plans during calls, address gaps in coverage - Use a customer-focused, needs-based review process to educate…

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Senior Tax Associate IN OFFICE

Company: River East Tax and Accounting Services Inc

Location: Chicago, IL

Posted Aug 17, 2025

Identify and implement tax planning strategies to minimize clients’ tax liabilities. Analyze financial data to determine the appropriate tax treatment of…

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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