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.

Grinder/Machine Operator

Company: Tool Steel Service

Location: Bridgeview, IL

Posted Aug 15, 2025

Light computer entry for processing orders. Machine Operators: run machines (grinding, sawing, milling equipment) to process steel products to meet customer…

View Details Apply on SimplyHired

Truck Driver CDL A Home Daily

Company: Ryder

Location: Chicago, IL

Posted Aug 15, 2025

Ensuring compliance with applicable federal and/or state laws, regulations, and/or agency rules, standards and guidelines. Ryder Drivers are Paid Weekly.

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Utilization Reviewer PRN-Behavioral Health Services

Company: Northwestern Medicine

Location: Chicago, IL

Posted Aug 15, 2025

Responsible for utilization review calls within BHS, including precertification, continued stay review, discharge reviews, and retrospective reviews and appeals…

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Electrician

Company: Tradesmen International, Inc.

Location: Chicago, IL

Posted Aug 15, 2025

Active Michigan Journeyman Electrician license. Ability to read and interpret electrical drawings and plans. Install electrical fixtures and related components.

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Armed Security Officer/Driver

Company: Kates Detective Agency

Location: Chicago, IL

Posted Aug 15, 2025

Remain in compliance with local, state, and federal regulations. This position involves patrolling client properties, ensuring safety, and driving company…

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Assistant Director, Communications and Digital Media

Company: The University of Chicago

Location: Chicago, IL

Posted Aug 15, 2025

Master’s degree in communications, journalism, creative arts (video), marketing, or related field. Familiarity with design tools such as Adobe Creative Suite,…

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Janitorial Overnight

Company: Walmart

Location: Villa Park, IL

Posted Aug 15, 2025

Programs range from high school completion to bachelor's degrees, including English Language Learning and short-form certificates.

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Building Service Supervisor

Company: University of Illinois

Location: Chicago, IL

Posted Aug 15, 2025

Supervise operations and activities of all custodial personnel engaged in cleaning and maintaining campus housing facilities for residents, guests and…

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Junior Sushi Chef

Company: Grain + Sea

Location: Chicago, IL

Posted Aug 15, 2025

Grain + Sea* is a modern, buffet-style sushi restaurant where guests build their perfect sushi box and pay by weight. Free staff meal during shift.

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Presentation Designer

Company: Rise

Location: Chicago, IL

Posted Aug 15, 2025

0–2 years of professional experience in visual design, presentation design, or a related creative field. You’ll work closely with strategists, planners, and…

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professional growth hospital part-time

RN - Wound Care - Per Diem Days

Company: Endeavor Health

Location: Chicago, Illinois

Posted Aug 15, 2025

View Details Apply on healthecareers.com

C++ Software Engineer

Company: Citadel Securities

Location: Chicago, IL

Posted Aug 15, 2025

Bachelor’s (or higher) degree in a Computer Science, Engineering or related field. Partner and Deliver: Collaborate directly with traders, researchers, and…

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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