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.

Director of Growth Marketing

Company: Four Seasons Heating And Air Conditioning Llc

Location: Bedford Park, IL

Posted Jul 23, 2025

As Director of Growth Marketing, you will own the strategy and execution of performance-driven acquisition channels—PPC, LSA, paid social, display/retargeting,…

CDL A Regional Driver - 100% no-touch freight

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

CDL A OTR Driver - get home weekly!

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

Regional CDL A Truck Driver: home at least weekly

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

Area Marketing Manager, Premium Select Hotels

Company: First Hospitality

Location: Chicago, IL

Posted Jul 23, 2025

Oversee portfolio social media efforts, driving following and engagement, fostering collaboration amongst broader marketing strategies.

Regional CDL A Truck Driver

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

Retail Sales Associate

Company: MY WIRELESS IL, INC

Location: Wood Dale, IL

Posted Jul 23, 2025

Experience prospecting through outbound calls. Training and developing your skills to become a top My Wireless Retail Sales Associate, which leads to…

Regional CDL A Driver - up to $105,000

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

Senior Manager, Organic Marketing

Company: Four Seasons Heating And Air Conditioning Llc

Location: Bedford Park, IL

Posted Jul 23, 2025

Coordinate with content team to develop service-specific blog posts, FAQs, landing pages, rich content, and CTAs that educate and drive action.

Sales Assistant Part Time

Company: Ralph Lauren

Location: Chicago, IL

Posted Jul 24, 2025

Interest in and appreciation for luxury and best-in-class service. Supports product pulls, fitting room setup & recovery, floor presentation standards and…

Second Shift Custodian

Company: Bennett Day School Inc

Location: Chicago, IL

Posted Jul 24, 2025

Bennett Day School is a progressive independent day school looking for passionate educators with an innovative spirit and rich background in learning and school…

Unarmed Security Officer

Company: American Heritage Protective Services, Inc.

Location: East Chicago, IN

Posted Jul 23, 2025

Receive all emergency and non-emergency incoming calls to the dispatch center while soliciting descriptive information to determine the nature and urgency of…

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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