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.

Owner Operator - CDL-A Flatbed Truck Driver

Company: Ace Doran

Location: Chicago, IL

Posted May 01, 2025

1 year of OTR/ Regional verifiable experience in the last 3 years or the same type of driving operation they are applying for. No age restrictions for tractors.

Senior HVAC Residential Service Technician

Company: Deljo Heating & Cooling

Location: Chicago, IL

Posted May 02, 2025

Valid driver's license and insurable driving record. Consult with customer on repair and replacements. Pay: $40.00 - $50.00 per hour depending on experience +…

Security and Safety Officer - Part Time

Company: Loyola University Health System

Location: Melrose Park, IL

Posted May 02, 2025

General - Valid Illinois driver's license. Specify Degree(s): Criminal Justice, Law Enforcement, Security Admin, Fire Services or related field.

Cashier

Company: Mariano's

Location: Chicago, IL

Posted May 05, 2025

Create an environment that enables customers to feel welcome, important and appreciated by answering questions regarding products sold within the department and…

CDL-A Truck Driver - Flatbed Division

Company: Koch Trucking

Location: Oak Park, IL

Posted May 02, 2025

All candidates must have a valid CDL-A license and 12 months of driving experience . Koch Trucking is looking to hire CDL-A truck drivers to join our flatbed…

CDL-A Solo & Team Owner Operator Truck Drivers

Company: Roadrunner

Location: Chicago, IL

Posted May 02, 2025

Connect with Roadrunner to experience the way truck driving business ownership should be. Average weekly pay averages between $2,500-$4,000 for solo drivers, $…

Cashier

Company: Mariano's

Location: Chicago, IL

Posted May 05, 2025

Create an environment that enables customers to feel welcome, important and appreciated by answering questions regarding products sold within the department and…

Retail Sales Associate

Company: Korn Ferry RPO for Tempur Sealy

Location: Oak Brook, IL

Posted May 03, 2025

During the first year of employment, your paid time off will be pro-rated based on date of hire unless otherwise dictated by state or local law.

Owner/Operator needed for Dedicated Line-Haul, Melrose Park, IL to Montpelier, OH

Company: BRYAN TRUCK LINE

Location: Melrose Park, IL

Posted May 02, 2025

Proven experience in truck driving with a strong understanding of commercial driving regulations. Ensure compliance with all federal, state, and local…

CDL-A Truck Driver - Flatbed Division

Company: Koch Trucking

Location: Cicero, IL

Posted May 02, 2025

All candidates must have a valid CDL-A license and 12 months of driving experience . Koch Trucking is looking to hire CDL-A truck drivers to join our flatbed…

Sr. Golang Software Engineer - Chicago, IL or Reston, VA- ONSITE -

Company: Comcast Corporation

Location: Chicago, IL

Posted May 05, 2025

Bachelor's or master's degree in computer science or a related field. Design and develop client-facing audience products, features, and applications using…

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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