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.

Piano Teacher (In-Home) - Full Health Benefits

Company: Piano Power

Location: Evanston, IL

Posted Aug 18, 2025

*You set your own teaching days and hours*, as long as you have at least two days a week to teach, you can make this a part-time or a full-time job.

PAINTER

Company: Cook County Health & Hospitals System

Location: Chicago, IL

Posted Aug 18, 2025

A copy of a valid State ID Card or Driver’s License which identifies the holder of the ID as a Veteran, may also be attached to the application at time of…

Principal Solution Architect - Data & Cloud Engineering

Company: Constellation Energy

Location: Chicago, IL

Posted Aug 18, 2025

Communicate data strategies and complex technical concepts clearly to both technical and non-technical stakeholders, fostering cross-functional collaboration…

On Call Hospice RN

Company: Oasis Hospice & Palliative Care, Inc.

Location: Chicago, IL

Posted Aug 18, 2025

Must be a licensed driver with an automobile that is insured in accordance with state of Illinois requirements and is in good working order.

Accounting Supervisor - Chicago IL, Loop

Company: Savant Wealth Management

Location: Chicago, IL

Posted Aug 18, 2025

*Lead with purpose:* Coach, develop, and empower a team of accountants, setting clear goals and aligning their efforts to Savant’s mission and strategic…

HVAC Field Supervisor/Turnover Technician

Company: Leslie Heating & Cooling

Location: Lombard, IL

Posted Aug 18, 2025

We need one (2) HVAC FIELD SUPERVISORS/TURNOVER Service Techs to help develop the growth of young talent and assist in generating leads for our sales department…

Class A CDL Owner Operator

Company: Trucking Edge

Location: Chicago, IL

Posted Aug 18, 2025

Earn 75% of line haul utilizing own trailer. 100% of billed fuel surcharge along with 100% of accessorials. Earn 70% of line haul revenue.

Registered Nurse

Company: Howard Brown Health

Location: Chicago, IL

Posted Aug 18, 2025

Nursing degree (BSN or Associates) PLUS current Illinois nursing license required; 1 to 2 years of experience in a hospital or outpatient setting is preferred.

Senior Manager - Global Payment Network Information Security Office (ISO) Consultant

Company: Capital One

Location: Chicago, IL

Posted Aug 18, 2025

Collaborating with enterprise cyber teams and tech architects in defining and driving the cyber architecture strategy and guiding principles for the…

Senior Business / Product Analyst

Company: Ryan Specialty

Location: Chicago, IL

Posted Aug 18, 2025

Heavily engaged in understanding and driving the required functionality of our digital distribution platforms as well as other peripheral systems.

Senior Manager - Global Payment Network Information Security Office (ISO) Consultant

Company: Capital One

Location: Chicago, IL

Posted Aug 18, 2025

Collaborating with enterprise cyber teams and tech architects in defining and driving the cyber architecture strategy and guiding principles for the…

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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