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.

CDL-A Regional Tanker Truck Driver

Company: TransWood

Location: Chicago, IL

Posted May 31, 2025

Good driving record with no major violations or accidents (some restrictions apply). 401(k) with employer matching. Hauling liquid chemicals in a liquid tanker.

Program Manager

Company: MATRIX PLASTIC PRODUCTS, LLC

Location: Wood Dale, IL

Posted Jun 03, 2025

The ideal candidate will be engineering-minded, have strong communication and organizational skills, patience, and a willingness to learn on the job.

Retail Sales and Store Support

Company: Jewel Osco

Location: Chicago, IL

Posted Jun 01, 2025

Health and welfare benefits for eligible employees (Medical, Dental, 401k and more!).

Class A Regional Driver- Champaign, IL

Company: Whiteline Express Ltd

Location: Chicago, IL

Posted May 31, 2025

Must meet DOT driving standards. Up to $0.12 per mile for driver referral program. Minimum of 6 months of Class A tractor/trailer experience within the past 24…

Temp Services Care Agent

Company: Lakeshore Recycling Systems LLC

Location: Rosemont, IL

Posted Jun 02, 2025

Take incoming sales calls to determine customer needs, provide proposals and close sales. Manage incoming internet leads through Salesforce and follow-up with…

2026 Commercial & Investment Bank Innovation Development Summer Analyst Program

Company: JPMorganChase

Location: Chicago, IL

Posted May 31, 2025

Problem-solving skills in interpreting data, trends, and insights to identify opportunities and develop actionable solutions. Analyze data to drive decisions.

Class A Regional Driver- Jackson Ctr, OH

Company: Whiteline Express Ltd

Location: Chicago, IL

Posted May 31, 2025

Must meet DOT driving standards. Up to $0.12 per mile for driver referral program. Minimum of 6 months of Class A tractor/trailer experience within the past 24…

Project Manager- Light Industrial Projects - Construction

Company: Michael Page

Location: Chicago, IL

Posted Jun 03, 2025

5+ years as a construction Project Manager for a commercial general contractor. Communicate regularly with owners, construction managers, other superintendents,…

Marketing Manager

Company: MillerKnoll

Location: Chicago, IL

Posted Jun 02, 2025

5–7 years in marketing or agency roles (advertising, PR, or integrated marketing); luxury, fashion, or design-focused brand experience preferred, with B2B or…

Plumber or Plumber Apprentice

Company: J Mac Mechanical

Location: Chicago Ridge, IL

Posted Jun 02, 2025

Must have own hand tools and a form of transportation to get to work. Must be able to listen to instruction and both work with others and by yourself.

CDL-A Independent Contractor Truck Driver

Company: TransAm Trucking

Location: Chicago, IL

Posted Jun 01, 2025

Must have at-least 12 months of verified tractor-trailer driving experience. No reckless driving violations in the last 5 years.

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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