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.

Customer Service Specialist

Company: PComm Direct

Location: Addison, IL

Posted Aug 30, 2025

Coordinate production of print projects, including working with sales, production and design teams to ensure all project aspects are aligned.

View Details Apply on SimplyHired

Customer Service & Sale Representative

Company: GLOBAL TALENT NEXUS

Location: Lombard, IL

Posted Aug 31, 2025

Tech-savvy with the ability to use CRM tools and reporting systems. Proactively manage assigned customer accounts and track progress toward retention goals.

View Details Apply on SimplyHired
full-time

Chair, Department of Obstetrics and Gynecology

Company: Loyola Medicine

Location: Chicago, Illinois

Posted Sep 01, 2025

View Details Apply on healthecareers.com

Customer Success Supervisor

Company: KO Business Solutions

Location: Elk Grove Village, IL

Posted Aug 31, 2025

High school diploma required; Bachelor’s degree in business or related field preferred. Familiarity with CRM systems and reporting tools.

View Details Apply on SimplyHired

Technical Accounting Manager

Company: Creative Financial Staffing

Location: Des Plaines, IL

Posted Aug 30, 2025

Salary range based off experience level, 130k-145k plus bonus. Work cross-functionally with Division CFO's and operating companies’ management, as well as…

View Details Apply on SimplyHired

Senior Brand Manager, Brand Growth & Innovation, Adult & Feminine Care

Company: Kimberly-Clark

Location: Chicago, IL

Posted Aug 31, 2025

Proven capability to lead in a matrix organization driving collaboration across businesses and functions. Strong understanding of brand foundational tools,…

View Details Apply on SimplyHired

CDLA Local Truck Drivers

Company: Calhoun Truck Lines

Location: Chicago, IL

Posted Sep 01, 2025

HOURLY PAY - $24 -$34 (Overtime after 40 hours) LOCAL RUNS - HOME DAILY! Weekends optional STEADY & STABLE WORK!

View Details Apply on SimplyHired

Sales and Merchandising Specialist

Company: SAS Retail Services

Location: Chicago, IL

Posted Sep 01, 2025

Have a valid driver’s license. You’re great at building relationships with store management, calling on customers and love the autonomy of managing your own…

View Details Apply on SimplyHired

SEC Reporting Manager

Company: Creative Financial Staffing

Location: Des Plaines, IL

Posted Aug 30, 2025

Salary range based off experience level, 130k-145k plus bonus. Work cross-functionally with Division CFO's and operating companies’ management, as well as…

View Details Apply on SimplyHired
full-time new grad academic

Academic Physicians - Child Abuse Pediatricians

Company: The University of Chicago

Location: Chicago, Illinois

Posted Aug 31, 2025

View Details Apply on healthecareers.com

Maintenance Electrician - Days B

Company: Sherwin-Williams

Location: Chicago, IL

Posted Sep 01, 2025

Have at least an industrial, electrical, and/or welding certifications or license. Understands basic electrical and pneumatic diagrams, familiar with 12 VDC to…

View Details Apply on SimplyHired

Customer Service Representative I

Company: Endeavor Health

Location: Chicago, IL

Posted Aug 29, 2025

Unique or Preferred Skills: Driver’s license. Answers a high volume of calls promptly ensuring outstanding customer service at all times.

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.

Related Pages

All Paid Time Off Jobs 23,177 jobs All Jobs in Chicago, IL 168,735 jobs Paid Time Off in Remote 1,246,135 jobs Paid Time Off in Other US Location 1,084,135 jobs Paid Time Off in New York City, NY 288,015 jobs Paid Time Off in Multiple Locations 253,625 jobs Paid Time Off in USA 227,410 jobs Paid Time Off in Washington DC 175,675 jobs Travel in Chicago, IL 79,837 jobs Full Time in Chicago, IL 46,687 jobs Retirement Plan in Chicago, IL 43,124 jobs 401(K) in Chicago, IL 37,542 jobs Health Insurance in Chicago, IL 34,384 jobs Life Insurance in Chicago, IL 33,039 jobs