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.

Electrical Estimator/Project Manager

Company: Arrow Flow

Location: Elk Grove, IL

Posted Jul 25, 2025

The ideal candidate will possess a strong background in electrical estimating, engineering, and project management, ensuring that all projects are completed on…

Payroll Accountant

Company: BGSF

Location: Chicago, IL

Posted Jul 25, 2025

Responsible for accurate tracking of global vacation and sick leave per Company policies and recording of financial liability by journal entry.

Project Delivery Manager (Warehouse/Mfg Automation exp. req. $140K)

Company: #twiceasnice Recruiting

Location: Chicago, IL

Posted Jul 25, 2025

Lead end-to-end delivery of warehouse automation projects, from design to implementation. Technical/automation solutions implementation: 3 years (Required).

Project Manager – Manufacturing and Technology

Company: Belden Universal

Location: Hillside, IL

Posted Jul 25, 2025

The Project Manager will lead and perform all phases of project management activities including scope management, requirements definition and analysis,…

Owner Operator Truck Driver – Intermodal Containers

Company: New Wave International Cargo, Inc

Location: Hodgkins, IL

Posted Jul 25, 2025

Valid CDL Class A license. Do you own your truck? The ideal candidate will own their truck, be familiar with container pick-ups and deliveries.

Teacher (2-Year-Olds) - (Must have Bachelors Degree in Early Childhood Edu.)

Company: Onward Neighborhood House

Location: Chicago, IL

Posted Jul 25, 2025

With the classroom team, ensure the implementation of the preschool program ensuring adherence to funding requirements as set by Head Start Program Performance…

Retail Sales - Women's Apparel - Old Orchard Center

Company: Nordstrom Inc

Location: Skokie, IL

Posted Jul 25, 2025

Set and achieve sales goals, for both in-store and digital selling with effective use of selling tools (inclusive of text and social media).

Centerless Grinding Machinist (Setup / Operator)

Company: Belden Universal

Location: Hillside, IL

Posted Jul 25, 2025

Sets up centerless grinding and honing equipment efficiently and effectively by entering instructions, including zero and reference points; setting tool…

HVAC Service Technician- LEAD EXPERIENCE- SIGN ON BONUS

Company: Home Comfort Services, Inc.

Location: Des Plaines, IL

Posted Jul 25, 2025

Valid driver's license with a clean driving record; van driving experience preferred. Proven experience as an HVAC Service or similar role in the field service…

Electrician/Machine Panel Wiring (5 yrs exp is +)

Company: Automatic Liquid Packaging Solutions (ALPS), LLC

Location: Arlington Heights, IL

Posted Jul 25, 2025

Read and understand electrical schematics (ladder diagrams) and mechanical layouts. Possesses a good understanding and fundamentals of electrical components (AC…

General Laborer

Company: Direct Line Communications INC

Location: Chicago, IL

Posted Jul 25, 2025

Use power tools and machinery as needed. Familiarity with power tools and machinery is a plus. Assist with erecting scaffolding and ladders.

Principal Solutions Architect, Banking & Capital Markets

Company: Chainlink Labs

Location: Chicago, IL

Posted Jul 25, 2025

Drive the successful adoption of Chainlink products in the capital markets industry by establishing strong relationships with key stakeholders, including major…

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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