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.

Truck Driver CDL A Home Daily

Company: Ryder

Location: Chicago, IL

Posted Aug 15, 2025

Ensuring compliance with applicable federal and/or state laws, regulations, and/or agency rules, standards and guidelines. Ryder Drivers are Paid Weekly.

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Electrician

Company: Tradesmen International, Inc.

Location: Chicago, IL

Posted Aug 15, 2025

Active Michigan Journeyman Electrician license. Ability to read and interpret electrical drawings and plans. Install electrical fixtures and related components.

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Registered Nurse, Pain Clinic

Company: Loyola University Health System

Location: Burr Ridge, IL

Posted Aug 15, 2025

Certification reimbursement (up to 1 certification). Develops and implements individualized care plans based on these assessments.

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Executive Sous Chef - Allstate Arena

Company: Aramark

Location: Rosemont, IL

Posted Aug 15, 2025

Interact directly with guests daily. Develop and maintain effective client and guest rapport for mutually beneficial business relationships.

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Project Accountant I

Company: Gilbane Building Company

Location: Chicago, IL

Posted Aug 15, 2025

Associate’s or Bachelor's degree in Accounting, Finance, Business, or a related field. Gilbane is seeking an Accountant I to assist the accounting staff in…

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Assistant Director, Communications and Digital Media

Company: The University of Chicago

Location: Chicago, IL

Posted Aug 15, 2025

Master’s degree in communications, journalism, creative arts (video), marketing, or related field. Familiarity with design tools such as Adobe Creative Suite,…

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Janitorial Overnight

Company: Walmart

Location: Villa Park, IL

Posted Aug 15, 2025

Programs range from high school completion to bachelor's degrees, including English Language Learning and short-form certificates.

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Custodian

Company: Giesecke+Devrient

Location: Bolingbrook, IL

Posted Aug 15, 2025

Use industrial walk-behind floor scrubber. Maintain cleanliness of floors, including sweeping, mopping, and waxing. High School Diploma or GED preferred.

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professional growth hospital part-time

RN - Wound Care - Per Diem Days

Company: Endeavor Health

Location: Chicago, Illinois

Posted Aug 15, 2025

View Details Apply on healthecareers.com

Customer Service Representative II

Company: Shure

Location: Niles, IL

Posted Aug 15, 2025

Fields entry level product related inquiries. Supports sales team by developing and maintaining positive customer relations, with clients/customers, which can…

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C++ Software Engineer

Company: Citadel Securities

Location: Chicago, IL

Posted Aug 15, 2025

Bachelor’s (or higher) degree in a Computer Science, Engineering or related field. Partner and Deliver: Collaborate directly with traders, researchers, and…

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FAS Pursuit Manager

Company: Deloitte

Location: Chicago, IL

Posted Aug 15, 2025

Collaborate with Technical Teams: Work with technical teams to develop clear, effective, and consistent content.

View Details Apply on SimplyHired

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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