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.

Service Plumber

Company: Deljo Heating and Cooling

Location: Chicago, IL

Posted Aug 25, 2025

Valid driver's license with an insurable driving record. 2+ years of plumbing field experience and installation experience. Willing to invest in tools.

Lead Software Engineer, Full stack

Company: Capital One

Location: Chicago, IL

Posted Aug 25, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

Wood Cabinet Assembler

Company: Quality Staffing, Inc.

Location: Bensenville, IL

Posted Aug 25, 2025

Capable of using basic hand tools and small power tools. Are you skilled in using basic hand tools and small power tools?

Seasonal Sales Associate

Company: Nespresso

Location: Chicago, IL

Posted Aug 25, 2025

As the welcoming face of our retail boutique, you will greet customers, offer complimentary coffee tastings, help with boutique operations and provide an…

Janitor

Company: The Community Builders

Location: Chicago, IL

Posted Aug 25, 2025

Constantly works in outdoor weather conditions. Frequently moves equipment weighing up to 50 pounds across sites. 403(b) retirement plan with company match.

Class A Commercial Driver

Company: CarMax

Location: Chicago, IL

Posted Aug 25, 2025

Valid state-issued commercial driver’s license Class A (CDL) Required. Except as otherwise required by state law, CarMax Associates are entitled to the…

Registered Nurse/Ultrasound Tech

Company: Women's Care Center

Location: Chicago, IL

Posted Aug 25, 2025

Our mission is simple: to help pregnant women from our communities choose life for their babies, have healthier pregnancies, become better parents and take…

Sous Chef

Company: Bazaar Meat by Jose Andres

Location: Chicago, IL

Posted Aug 25, 2025

Train and develop kitchen staff; train cooks/kitchen staff in the importance of consistency in preparation and presentation.

CDL-A Company Driver

Company: Dollar General

Location: Chicago, IL

Posted Aug 25, 2025

1+ years CDL A driving experience. Must be 21 years of age. Experience preferred, requirement based on location. Short term and long term disability.

Senior Real Estate Accountant

Company: RE/MAX Premier

Location: Chicago, IL

Posted Aug 25, 2025

*Bachelor’s degree* in Accounting, Finance, or related field (CPA or advanced designation preferred). The *Lead Accountant* will be responsible for managing the…

Enrichment Teacher (Project Tree)

Company: Evergreen Park School District 124

Location: Evergreen Park, IL

Posted Aug 25, 2025

Collaborates with administration, classroom teachers, Project Tree teachers and parents. Maintains complete and accurate records of student’s progress and…

HVAC Service Technician/ Installer

Company: Precision Heating and Cooling

Location: Alsip, IL

Posted Aug 25, 2025

Come and join the area's premier Heating and Air Conditioning contractor. We offer year round work as well as a complete and excellent benefits package.

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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