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.

Lead Preschool Teacher

Company: St. Thomas The Apostle School

Location: Chicago, IL

Posted Apr 28, 2025

The ideal candidate will have a strong background in Active Playful Learning, 21st Century learning and a student centered philosophy.

View Details Apply on SimplyHired

Lead Software Engineer (C++ AND Golang) On-site, Chicago, IL or Reston, VA

Company: Comcast Corporation

Location: Chicago, IL

Posted Apr 29, 2025

Oversees the researching, writing and editing of documentation and technical requirements, including software designs, evaluation plans, test results, technical…

View Details Apply on SimplyHired

CNC Swiss Set Up/Operator

Company: Precision-Tek Mfg., Inc

Location: Arlington Heights, IL

Posted Apr 29, 2025

Ability to read technical drawings and blueprints effectively. Operate CNC machines and equipment to manufacture parts as per technical drawings and…

View Details Apply on SimplyHired

Chef de Cuisine

Company: The Oakville Grill & Cellar

Location: Chicago, IL

Posted Apr 29, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

View Details Apply on SimplyHired

Sous Chef

Company: The Oakville Grill & Cellar

Location: Chicago, IL

Posted Apr 29, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

View Details Apply on SimplyHired
relocation assistance staffing agency contract

Travel CT Technologist - $2,652 per week

Company: Focus Staff

Location: Chicago, Illinois

Posted Apr 29, 2025

View Details Apply on healthecareers.com

Plumber

Company: THE PLUMBING DEPARTMENT INC

Location: Chicago, IL

Posted Apr 30, 2025

Running service calls that include assembly/installation and repair of plumbing, water flow, and drainage systems in accordance with plumbing codes.

View Details Apply on SimplyHired

HVAC Technician

Company: Topline HVAC

Location: Skokie, IL

Posted Apr 29, 2025

You will install, service, and repair heating and air conditioning systems. Familiarity with HVAC wiring diagrams. Respond to emergency maintenance requests.

View Details Apply on SimplyHired

Data Control Officer | Security (Access Control)

Company: Sitemetric

Location: Elk Grove Village, IL

Posted Apr 28, 2025

Sitemetric provides construction owners, general contractors, subcontractors, and workers data, hardware, software, and tech-enabled services in combinations…

View Details Apply on SimplyHired

Executive Sous Chef

Company: The Oakville Grill & Cellar

Location: Chicago, IL

Posted Apr 29, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

View Details Apply on SimplyHired

HVAC/R Service Technician - Light Commercial

Company: CoolSys

Location: Chicago, IL

Posted Apr 30, 2025

Sr, senior, Service Tech, refridgeration, HVAC, refrigeration, HVAC-R, HVAC/R, diagnostic, commercial, service, install, mechanical, mechanic, apprentice, AC,…

View Details Apply on SimplyHired

HVAC/R Service Technician - Light Commercial

Company: CoolSys

Location: Oak Lawn, IL

Posted Apr 30, 2025

Sr, senior, Service Tech, refridgeration, HVAC, refrigeration, HVAC-R, HVAC/R, diagnostic, commercial, service, install, mechanical, mechanic, apprentice, AC,…

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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