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.

Executive Sous Chef

Company: Gibson's Bar & Steakhouse- Rosemont

Location: Rosemont, IL

Posted Aug 08, 2025

Hire, train, supervise, and develop kitchen staff. Ensure all kitchen and food operations are in compliance with all legislated health and licensing guidelines;…

Customer Service Representative

Company: Continental Western Corporation

Location: Chicago, IL

Posted Aug 08, 2025

Manage large amounts of incoming calls. Provide accurate, valid and complete information by using the right methods/tools. Track record of over-achieving quota.

Full-Time Multimarket Customer Service Agent

Company: H&M Group

Location: Chicago, IL

Posted Aug 08, 2025

Ability to work at a fast pace, multitask and manage fluctuations in workload handling multiple chats and calls at the same time. Health and Dependent Care FSA.

Security Call Off Coverage - Entry Level

Company: GardaWorld Security Services U.S.

Location: Lombard, IL

Posted Aug 08, 2025

A comprehensive benefits package including medical, dental, and vision insurance plans, a 401(k) retirement savings plan with employer matching contributions,…

Epoxy Floor Technician / Crew Leader

Company: Comer & Cross Coatings

Location: Elk Grove Village, IL

Posted Aug 08, 2025

Trailer driving experience a plus! Driving work truck to and from work sites, if applicable. Proper and satisfactory completion of projects including prep,…

Apprentice Cybersecurity Analyst

Company: Catalyte

Location: Chicago, IL

Posted Aug 08, 2025

Its proprietary technology uses 200K data points to discover and develop high-potential talent. Fast track your entry into the cybersecurity industry with…

Janitor - evening - Commercial Bldg

Company: Monadnock Building

Location: Chicago, IL

Posted Aug 08, 2025

Keep areas clean, including stairs, interior sills and hardware. The Janitor is responsible for cleaning the lobby, restrooms, and common areas, and daily…

Wireless Retail Sales Associate

Company: Mobile Generation - Verizon Premium Retailer

Location: Evanston, IL

Posted Aug 08, 2025

The ideal candidate will have experience in retail environments, understand how to do outbound activities to drive customers into our locations, are driven by…

Maintenance Technician/Electrician (2nd & 3rd Shift)

Company: The Royal Group

Location: Cicero, IL

Posted Aug 08, 2025

High school diploma or equivalent; technical certification or apprenticeship in mechanical or electrical trades preferred.

Automotive Controller- Luxury

Company: Ed Napleton Automotive Group

Location: Chicago, IL

Posted Aug 08, 2025

18+ years of age or older to comply with the company driving policy. Ability to explain technical financial information in an understandable manner.

Security Supervisor - Special Response

Company: GardaWorld Security Services U.S.

Location: Chicago, IL

Posted Aug 08, 2025

A comprehensive benefits package including medical, dental, and vision insurance plans, a 401(k) retirement savings plan with employer matching contributions,…

Hourly (K-8)

Company: Chicago Public Schools

Location: Chicago, IL

Posted Aug 08, 2025

Data entry, filing, answering phones and other various clerical duties. Our vision is that Every Chicago Public Schools student in every neighborhood will be…

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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