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.

Jr. Graphic Designer

Company: CannonDesign

Location: Chicago, IL

Posted Jul 29, 2025

Bachelor's degree in graphic design or a related field. 1+ years professional experience in a graphic design position, experience in the AE field is a plus but…

Regional Dry Van Truck Driver

Company: Roehl Transport

Location: Chicago, IL

Posted Jul 29, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,330/week. *Home weekly* – typically for 48 hours.

Full-Time Custodian

Company: Legacy Charter School

Location: Chicago, IL

Posted Jul 29, 2025

Our mission is to create an outstanding center for teaching and learning for children and their families that will recognize and nurture the full potential of…

executive Chef

Company: Rosebud Restaurants

Location: Chicago, IL

Posted Jul 29, 2025

Candidates should be able to perform calmly and effectively in a fast-paced environment, be an efficient multi-tasker, maintain a positive attitude and friendly…

Customer Service Representative

Company: Respire Homecare

Location: Elmhurst, IL

Posted Jul 29, 2025

Answers incoming phone calls promptly and courteously. Answer phone calls by the 2nd ring, Receive, qualify, and process, according to procedure, all customer…

Truck Driver (Reefer): up to $1600+ per week

Company: Roehl Transport

Location: Chicago, IL

Posted Jul 29, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,365/week. *Home weekly* – typically for 48 hours.

Production, Graphic Design

Company: International Interior Design Association

Location: Chicago, IL

Posted Jul 29, 2025

Work experience at a marketing/advertising agency or within architecture, interior design, environmental design, or multidisciplinary design firms.

SUPERVISING WATCHMAN

Company: City of Chicago

Location: Chicago, IL

Posted Jul 29, 2025

NOTE: A valid State of Illinois driver's license is required. Receives scheduled calls from Watchmen reporting in from their locations and calls from city…

HVAC/R Technician II

Company: 7-Eleven

Location: Rosemont, IL

Posted Jul 29, 2025

Respond to service requests for HVAC, refrigeration, cold beverage equipment, ice makers, in addition to work orders related to plumbing, electrical, and…

Cabinet Assembly and Laminating

Company: Cabinets Unlimited Inc

Location: Bensenville, IL

Posted Jul 29, 2025

Applicant must be safety conscious, able to read a tape measure, have basic hand tools, able to work in a manufacturing environment, and able to lift up to 75…

LEAD ACCOUNTANT

Company: City of Chicago

Location: Chicago, IL

Posted Jul 29, 2025

Graduation from an accredited college or university with a Bachelor's degree in Accounting or a directly related field with 15 credit hours in Accounting, plus…

Project Manager

Company: Duly Health and Care

Location: Downers Grove, IL

Posted Jul 29, 2025

Bachelor’s degree in Information Systems, Business, Healthcare Administration, or related field. These roles are critical to managing project lifecycles across…

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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