Generous Paid Time Off Jobs in Chicago, IL

73,230 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.

Backend Software Engineer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Feb 21, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

View Details Apply on SimplyHired

Pharmacist-Drug Diversion Surveillance Analyst, Full-time Days

Company: Northwestern Medicine

Location: Chicago, IL

Posted Feb 20, 2025

We consider this on a case-by-case basis and follow all state and federal guidelines. We offer a wide range of benefits that provide employees with tools and…

View Details Apply on SimplyHired
hospital travel

Travel Registered Respiratory Therapist - $2,065 per week

Company: Ann & Robert H. Lurie Childrens Hospital of Chicago

Location: Chicago, Illinois

Posted Feb 18, 2025

View Details Apply on healthecareers.com
contract travel health insurance

Travel Nurse RN - Bone Marrow Transplant - $2,494 per week

Company: Stability Healthcare

Location: Chicago, Illinois

Posted Feb 19, 2025

View Details Apply on healthecareers.com

Senior Director, Insurance Institutional Sales

Company: The Federal Home Loan Bank of Chicago

Location: Chicago, IL

Posted Feb 18, 2025

Drive Business Growth: By developing and executing strategic account plans, you’ll directly contribute to meeting sales objectives and driving significant…

View Details Apply on SimplyHired

Registered Nurse, Family Practice

Company: Loyola University Health System

Location: Berwyn, IL

Posted Feb 20, 2025

Certification reimbursement (up to 1 certification). Develops and implements individualized care plans based on these assessments.

View Details Apply on SimplyHired
prn retirement plan tuition reimbursement

Home Health Occupational Therapist - $94K+ per year

Company: LHC Group

Location: Chicago Heights, Illinois

Posted Feb 19, 2025

View Details Apply on healthecareers.com
travel health savings account life insurance

Travel Respiratory Therapist - $2,201 per week

Company: Host Healthcare

Location: Chicago, Illinois

Posted Feb 18, 2025

View Details Apply on healthecareers.com
travel 401(k) life insurance

Travel Nurse RN - Telemetry PCU - Progressive Care Unit - $2,064 per week

Company: American Traveler

Location: Chicago, Illinois

Posted Feb 18, 2025

View Details Apply on healthecareers.com
contract travel health savings account

Local Contract Cath Lab Technologist - $59-67 per hour

Company: Host Healthcare

Location: Chicago, Illinois

Posted Feb 19, 2025

View Details Apply on healthecareers.com
travel 401(k) life insurance

Travel Nurse RN - ICU - Intensive Care Unit - $2,280 per week

Company: American Traveler

Location: Chicago, Illinois

Posted Feb 18, 2025

View Details Apply on healthecareers.com

Registered Nurse

Company: DAVITA

Location: Chicago, IL

Posted Feb 19, 2025

Comprehensive benefits: medical, dental, vision, 401k, paid time off, PTO cash out, DaVita-negotiated discounts on hundreds of items from your cell phone plan…

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