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.

Electrician

Company: Four Seasons Heating And Air Conditioning Llc

Location: Bridgeview, IL

Posted Jul 30, 2025

Requirements: Minimum of 3 years of electrical experience required; should be adept in residential service upgrades and generator installs, as well as have…

Enterprise Product Risk Lifecycle Analyst

Company: paypal

Location: Chicago, IL

Posted Jul 30, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

Licensed Customer Service Representative- Insurance Agency

Company: Allstate Insurance - Jackson and Associate Agency

Location: Chicago, IL

Posted Jul 30, 2025

Utilize agency tools and technology to track customer interactions and follow-ups. *Hands-On Training & Licensing Support* (if not already licensed).

Machine Operator 1st and 2nd Shift

Company: JobSquad Staffing Solutions

Location: Stone Park, IL

Posted Jul 30, 2025

Responsible for manufacturing, distributing and consistently maintaining safe and quality food by following good manufacturing practices, allergen controls,…

Enterprise Product Risk Lifecycle Analyst

Company: PayPal

Location: Chicago, IL

Posted Jul 31, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

Customer Service Coordinator - Level 2

Company: AVLON INDUSTRIES

Location: Melrose Park, IL

Posted Jul 30, 2025

Associate or bachelor’s degree or equivalent experience. Customer service : 2 years (Required). 2-4 years of experience in customer service, order processing,…

Residential Security Officer MPP

Company: Securatex

Location: Chicago, IL

Posted Jul 30, 2025

The ideal candidate will be experienced in security operations, have strong communication skills, and be able to handle various tasks such as package management…

Officer (8AM-4PM Shift)

Company: Art Institute of Chicago

Location: Chicago, IL

Posted Jul 31, 2025

Works regularly in all Control areas; inspects parcels, issues keys, visitor and contractor management, answering radio traffic and telephones, etc.

Manager, Customer Success

Company: Intercom

Location: Chicago, IL

Posted Jul 30, 2025

You will internally influence cross-functional partners to ensure we are driving positive customer outcomes. 2+ years of experience in a leadership role within…

Welder (Madison) 2nd Shift

Company: Hydro, Inc.

Location: Chicago, IL

Posted Jul 30, 2025

Welding certification in 6g, a plus. You will be responsible for setting up and operating a variety of welding equipment, including an electric-welding…

Full-Stack Engineer / .NET and React / On-Site / Wheaton, IL

Company: Motion Recruitment

Location: Chicago, IL

Posted Jul 30, 2025

The engineer will be responsible for implementing new features, resolving technical issues, and ensuring the applications stay current with industry trends.

Recruiting Manager (Robert Half Marketing & Creative)

Company: Robert Half

Location: Chicago, IL

Posted Jul 30, 2025

As a Recruiting Manager, your responsibilities will include developing and growing a client base and new business opportunities, introducing our services via…

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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