Generous Paid Time Off Jobs in Chicago, IL

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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.

Compensation Analyst

Company: Anchor Staffing, Inc.

Location: Chicago, IL

Posted Apr 01, 2025

Reporting to the Director-Compensation, the *Compensation Analyst* assists in administering employee compensation programs, which includes: creating position…

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Special Education Teacher- 2025-2026

Company: Onward Search Education

Location: Berwyn, IL

Posted Apr 02, 2025

Maintain accurate student records and communicate progress with parents and school administrators. Monitor and assess students’ progress toward IEP goals and…

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Research Analyst

Company: The University of Chicago

Location: Chicago, IL

Posted Apr 01, 2025

Minimum requirements include a college or university degree in related field. Bachelor’s Degree in economics or related quantitative field.

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Electrical and Instrumentation Technician

Company: Alsip MiniMill, LLC

Location: Alsip, IL

Posted Apr 04, 2025

Demonstrated competence in heavy industrial continuous-process environment (i.e., oil refinery, chemical plant, power plant, etc.). Life/ADD, STD/LTD Insurance.

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HVAC Service Tech

Company: American Vintage Home

Location: Evanston, IL

Posted Apr 04, 2025

Valid drivers license with a safe driving record. 2+ years of field experience. Diagnose, troubleshoot, and repair HVAC systems, including forced air and…

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UACL LOOKING FOR VAN LOCAL & REGIONAL OWNER OPERATOR

Company: UACL Logistics, LLC

Location: Chicago, IL

Posted Apr 04, 2025

6 Months free trailer rental. \*\* UACL LOOKING FOR VAN OWNER OPERATORS\*\**. Route is going from Chicago, IL to OH, OK, MI, LA. What it takes to join our team:

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RETAIL SALES CONSULTANT - The Dump Luxe Furniture Outlet

Company: NEW VENTURE HOLDINGS, LLC

Location: Lombard, IL

Posted Apr 03, 2025

We will provide you with a Training Program and your own Sales Coach to help you learn the ropes, hone your skills, and become a sales superstar in no time.

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Plumber - Residential

Company: American Vintage Home

Location: Evanston, IL

Posted Apr 04, 2025

Valid drivers license with a safe driving record. 2+ years of field experience. Ability to troubleshoot, repair, and collect payment.

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Carpenter

Company: Kehoe Designs Inc

Location: Chicago, IL

Posted Apr 02, 2025

Proficient in using a variety of hand tools (hammers, screwdrivers, drills, staple guns, tape measure) and power tools (table saw, jigsaw, chop saw, router,…

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Project Manager, Construction

Company: Wheatland Tube, LLC

Location: Chicago, IL

Posted Apr 03, 2025

Leads cross-functional teams, including construction, logistics, design/engineering, and manufacturing groups – Coordinates all stakeholders for seamless…

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travel health savings account life insurance

Travel Cath Lab Technician - $2,434 per week

Company: Host Healthcare

Location: Chicago, Illinois

Posted Apr 05, 2025

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

Travel Nurse RN - ICU - Intensive Care Unit - $2,025 per week

Company: Cross Country Nurses

Location: East Chicago, Indiana

Posted Apr 06, 2025

View Details Apply on healthecareers.com

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.

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