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.

Assistant Project Manager

Company: J. F. Ahern Co.

Location: Chicago, IL

Posted Jul 22, 2025

You will be a key member on the project team making sure field crews have their resources well planned and organized for installation efficiency.

Senior Software Development Engineer

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 22, 2025

Minimum requirements include a college or university degree in related field. Solves complex problems and identifies opportunities for technical improvement and…

Executive Chef – High-Profile Rooftop Venue

Company: Artifact Events

Location: Chicago, IL

Posted Jul 22, 2025

This role is ideal for a hands-on leader who thrives in high-volume, high-visibility environments and is passionate about driving excellence across food, people…

ACCOUNTANT

Company: SGA YOUTH & FAMILY SERVICES NFP

Location: Chicago, IL

Posted Jul 22, 2025

Perform accounting, clerical and analytical tasks related to the efficient bookkeeping maintenance and processing of accounts payable / account receivable…

Graphic Designer/Marketing

Company: American Classic Tours

Location: Des Plaines, IL

Posted Jul 22, 2025

Social Media Marketing: schedule and post engaging content across our social media platforms. Email Marketing: design weekly eblasts sent to our travelers…

Temporary Teacher (PreK-3)

Company: Chicago Public Schools

Location: Chicago, IL

Posted Jul 22, 2025

ESSENTIAL FUNCTIONS: Responsible for instructional planning, including, but not limited to, providing written lesson plans and preparation in accordance with…

Owner Operator Truck Driver

Company: TForce Freight Inc

Location: Chicago, IL

Posted Jul 22, 2025

Join TForce Freight and enjoy a work environment that exceeds your Class A truck driver business needs and those of your family! Solos- up to 3,000 miles/week.

Machine Learning Engineer

Company: BMO US

Location: Chicago, IL

Posted Jul 22, 2025

Works with other data and analytics professionals to optimize, refine, automate and scale analysis into repeatable analytics solutions and decision support…

Indirect Tax Sales & Use Manager--Open Location

Company: EY

Location: Chicago, IL

Posted Jul 22, 2025

Under our flexible vacation policy, you’ll decide how much vacation time you need based on your own personal circumstances.

Bilingual Security Officer (Part-Time)

Company: Chicago Children's Advocacy Center

Location: Chicago, IL

Posted Jul 22, 2025

Answer telephone calls to take messages or determining appropriate staff member to forward calls to. The Security Officer will greet all visitors according to…

Welder

Company: AVW Equipment

Location: Maywood, IL

Posted Jul 22, 2025

Analyzes blueprints, plans, and drawings to determine measurements, plan layout, and sequence of welding assignments. Must pass a weld test.

CNC Machinist III, 1st shift

Company: Regal Rexnord

Location: Downers Grove, IL

Posted Jul 22, 2025

Person’, which includes U.S. citizens, U.S. nationals, U.S. permanent residents, individuals granted asylum in the United States, and refugees in the United…

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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