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.

Bathroom Remodeling Installer

Company: J. Blanton Plumbing

Location: Northbrook, IL

Posted Jul 07, 2025

Valid plumbing license or current apprenticeship status (apprenticeship sponsorship available). Read and interpret blueprints and technical drawings for…

Data Scientist (Hybrid)

Company: Enova International

Location: Chicago, IL

Posted Jul 07, 2025

At times, you may be asked to conduct ad hoc analysis using statistical and financial tools to recommend for risk management, marketing and operational…

Manager, Media Planning (Traditional and Digital)

Company: Rise

Location: Chicago, IL

Posted Jul 07, 2025

Develop and oversee media strategy, campaign creation, budget, optimization, and testing strategy(ies), as applicable, for full-funnel, multi-platform campaigns…

Rocker Framer

Company: E&K of Chicago, Inc.

Location: Elmhurst, IL

Posted Jul 05, 2025

Screw guns, routers, chop saws, powder actuated tools (Hilti), various hand tools, knives and lasers. From (1") to (48"), (20/day), a distance of up to (20 feet…

2nd Shift CNC Machinist

Company: OPW

Location: Skokie, IL

Posted Jul 07, 2025

Benefits: Our total rewards package for eligible team members also includes: a 401(k) savings plan with employer contributions; medical, dental and vision…

Staff Nurse

Company: Union Health Service

Location: Chicago, IL

Posted Jul 07, 2025

Under the direction of the Charge Nurse, the Staff Nurse provides ambulatory care services to patients in all age groups, working with primary care and…

Senior Brand Manager - Cottonelle® Flushable Wipes

Company: Kimberly-Clark

Location: Chicago, IL

Posted Jul 06, 2025

Diverse income protection insurance options to protect yourself and your family in case of illness, injury, or other unexpected events. In this role, you will:

Retail Sales Associate

Company: The Hireverse

Location: Rosemont, IL

Posted Jul 07, 2025

As a *Retail Sales Associate*, you will play a key role in driving sales and providing outstanding customer service.

HVAC Service Technician

Company: Guardian Heating & Cooling Services LLC

Location: Chicago, IL

Posted Jul 07, 2025

Valid driver's license and insurable driving record. Service / maintenance / repair on residential heating and air conditioning systems.

Permanent Substitute Teacher

Company: Oak Park Elementary School District 97

Location: Oak Park, IL

Posted Jul 06, 2025

They establish a positive rapport with students, motivating them to develop the skills, attitudes, and knowledge needed to pursue their full potential.

Controller/Accountant Automotive Dealership

Company: Confidential Car Dealership

Location: Chicago, IL

Posted Jul 07, 2025

Bachelor's degree in Accounting, Finance, or related field; CPA or CMA preferred. Manage the financial planning and analysis process, including forecasting,…

Project Manager

Company: Michael Page

Location: Chicago, IL

Posted Jul 06, 2025

The Project Manager is responsible for scheduling, oversight of construction and communication with project team. Bonus per project (up to 12%).

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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