Generous Paid Time Off Jobs in Chicago, IL

73,229 open positions · Updated daily

Looking for Generous Paid Time Off jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Generous 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
relocation assistance sign-on bonus health system

Join our established Endocrinology team in South Chicago

Company: Advocate Health

Location: Chicago, Illinois

Posted Apr 27, 2025

View Details Apply on healthecareers.com

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
staffing agency contract travel

Travel Respiratory Therapist - $1,726 per week

Company: MedPro Healthcare Allied Staffing

Location: Chicago, Illinois

Posted Apr 28, 2025

View Details Apply on healthecareers.com
travel life insurance retirement plan

Travel CT Technologist - $2,464 per week

Company: GetMed Staffing, Inc.

Location: Chicago, Illinois

Posted Apr 27, 2025

View Details Apply on healthecareers.com
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
staffing agency contract travel

Travel Nurse RN - Interventional Radiology - $2,735 per week

Company: MedPro Healthcare Staffing

Location: Chicago, Illinois

Posted Apr 28, 2025

View Details Apply on healthecareers.com

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
full time academic

Academic Physicians - Pediatric Pulmonologists

Company: The University of Chicago

Location: Chicago, Illinois

Posted Apr 27, 2025

View Details Apply on healthecareers.com
malpractice insurance paid time off relocation assistance

Minimally Invasive Surgery - Chief

Company: Trinity Health

Location: Chicago, Illinois

Posted Apr 28, 2025

View Details Apply on healthecareers.com
travel life insurance retirement plan

Travel Telemetry RN - $1,373 per week

Company: GetMed Staffing, Inc.

Location: Chicago, Illinois

Posted Apr 27, 2025

View Details Apply on healthecareers.com

Retail Sales and Store Support

Company: Jewel Osco

Location: Chicago, IL

Posted Apr 28, 2025

Health and welfare benefits for eligible employees (Medical, Dental, 401k and more!).

View Details Apply on SimplyHired

Frequently Asked Questions

What are the typical salary ranges for Generous PTO roles by seniority?
Entry‑Level PTO Analyst: $55k–$70k; Mid‑Level PTO Manager: $80k–$110k; Senior PTO Director: $130k–$170k. These ranges vary by region and company size.
Which skills and certifications are required for Generous PTO positions?
Core skills: PTO policy design, HRIS configuration (Workday, SAP SuccessFactors), data analytics (SQL, Excel, Power BI), compliance knowledge (FERPA, GDPR). Certifications: SHRM‑CP/SHRM‑SCP, HRIS Certified Professional, Workday HCM Certification, SAP SuccessFactors HCM Certification.
Is remote work available for Generous PTO roles?
Approximately 70% of PTO analyst and benefits coordinator positions allow full‑time remote or hybrid work, especially in SaaS and tech firms. On‑site roles exist for compliance audit positions that require physical access to employee records.
What are the career progression paths in Generous PTO roles?
PTO Analyst → PTO Manager → PTO Director → HR Director / VP of People Experience → Chief People Officer. Each step expands strategic influence from policy design to workforce planning.
What are the current industry trends for Generous PTO?
AI‑driven leave analytics, continuous PTO policies, integration of mental‑health metrics, global time‑zone‑aware accrual systems, emphasis on employee well‑being dashboards. Companies are adopting flexible PTO models to attract and retain talent.

Related Pages

All Generous Paid Time Off Jobs 2,162 jobs All Jobs in Chicago, IL 472,458 jobs Generous Paid Time Off in Remote 3,489,178 jobs Generous Paid Time Off in Other US Location 3,035,578 jobs Generous Paid Time Off in New York City, NY 806,442 jobs Generous Paid Time Off in Multiple Locations 710,150 jobs Generous Paid Time Off in USA 636,748 jobs Generous Paid Time Off in Washington DC 491,890 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