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.

Housekeeping Attendant

Company: East Bank Club

Location: Chicago, IL

Posted Aug 14, 2025

The Locker Room Housekeeping Attendant will help foster the culture of East Bank Club by maintaining a clean, organized, and fully stocked locker room while…

View Details Apply on SimplyHired

Project Manager

Company: Ryan Specialty

Location: Chicago, IL

Posted Aug 14, 2025

Identifies potential risks and develops mitigation strategies monitoring and managing risks throughout the project lifecycle.

View Details Apply on SimplyHired

Industrial Electrician

Company: Maintenance Engineering Solutions

Location: Alsip, IL

Posted Aug 14, 2025

We are currently seeking an experienced Industrial Electrician who will be responsible for supporting plant operations by troubleshooting, repairing, replacing,…

View Details Apply on SimplyHired

Staff Accountant

Company: Dhaliwal Labs

Location: Bedford Park, IL

Posted Aug 14, 2025

Ideally, the candidate will be qualified to a bachelor’s degree level. Conduct financial analysis to identify trends, variances, and opportunities for…

View Details Apply on SimplyHired
full-time

Clinical Associates - Transplant Hepatology

Company: The University of Chicago

Location: Chicago, Illinois

Posted Aug 14, 2025

View Details Apply on healthecareers.com

Registered Nurse (RN)

Company: ALIYA on 87th

Location: Chicago, IL

Posted Aug 14, 2025

Active Registered Nurse (RN) license in the state of Illinois. Collaborate with allied health team members to develop and implement individualized care plans.

View Details Apply on SimplyHired

Promotional Products Subject Matter Expert

Company: Main St.

Location: Chicago, IL

Posted Aug 14, 2025

Main Street delivers impactful brand stories through design, displays, promotional, print, packaging, and fulfillment. Ability to travel 20% of the time.

View Details Apply on SimplyHired

Licensed Special Education Teacher (SPED)

Company: Healthpro Heritage, LLC

Location: Cicero, IL

Posted Aug 14, 2025

Must hold a current license to practice in the state of ?state. Conduct initial screenings as well as comprehensive evaluations Participate in the IEP process…

View Details Apply on SimplyHired

EXECUTIVE SOUS CHEF

Company: Culinaire

Location: Chicago, IL

Posted Aug 14, 2025

Recognized as the technical expert, teacher and trainer for this operation and the culinary team. Current and cutting edge on new products, presentations, and…

View Details Apply on SimplyHired

Police Officer (Active or Retired)

Company: ACCEL ENTERTAINMENT

Location: Wheeling, IL

Posted Aug 14, 2025

Valid driver’s license; clean driving record. The primary duties of this position include, but are not limited to, providing safety and security to employees…

View Details Apply on SimplyHired

CDL A Flatbed Truck Driver - Home Weekly

Company: AWL Transport Inc. dba TLX

Location: Chicago, IL

Posted Aug 14, 2025

2 Years Verifiable Driving Experience w/ Steel coil & heavy haul experience. Must be 22 Years of Age. OUR FLATBED TRUCK DRIVERS EARN UP TO $80,000 PER YEAR –…

View Details Apply on SimplyHired

Construction Project Manager

Company: Evergreen Real Estate Services Llc

Location: Chicago, IL

Posted Aug 14, 2025

Valid driver’s license required. Bachelor’s degree in Construction Management, Civil Engineering, Architecture, or related field required.

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 236,229 jobs Paid Time Off in Remote 1,744,589 jobs Paid Time Off in Other US Location 1,517,789 jobs Paid Time Off in New York City, NY 403,221 jobs Paid Time Off in Multiple Locations 355,075 jobs Paid Time Off in USA 318,374 jobs Paid Time Off in Washington DC 245,945 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