Paid Time Off Jobs in Chicago, IL

72,501 open positions · Updated daily

Looking for Paid Time Off jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Paid Time Off position in the Chicago, IL area.

CDL-A Driver - Home Daily

Company: Venture Transport

Location: Cicero, IL

Posted Oct 08, 2025

$2,500 unlimited driver referral bonus. At Venture Transport, you’re more than just a driver—you’re the backbone of our success. 9 months in the past 3 years.

View Details Apply on SimplyHired

Armed Security Guard

Company: GARDAWORLD FEDERAL SERVICES LLC

Location: Norridge, IL

Posted Oct 08, 2025

Must possess a valid driver's license and reliable transportation to the assigned site. Must possess and maintain an active State Security Guard License for the…

View Details Apply on SimplyHired

MARKETING MANAGER

Company: Eurest

Location: Elmhurst, IL

Posted Oct 07, 2025

Holiday Time Off (varies by site/state). Associates may also be eligible for paid and/or unpaid time off benefits in accordance with applicable federal, state,…

View Details Apply on SimplyHired

2nd Shift CNC Machinist (10% Shift Diff - Direct Hire)

Company: Arsenal Recruiting

Location: Elk Grove Village, IL

Posted Oct 07, 2025

CNC Mill Experience (3-5 Axis). Fanuc, Siemens or Okuma experience preferred. Comfortable editing G & M codes. -10% Shift Differential for 2nd Shift!*.

View Details Apply on SimplyHired

Machine Operator/Welder

Company: All Steel Structures, Inc.

Location: South Holland, IL

Posted Oct 08, 2025

Experienced Structural Welder Accurate Blue Print Reading Capable of 3G certification Mig Welding Torch Cutting Grinding and Buffing steel Lay-out &…

View Details Apply on SimplyHired

Software Engineer

Company: Spraying Systems Co

Location: Glendale Heights, IL

Posted Oct 07, 2025

*Modern Tooling*: Utilize tools like *Git* for version control and AI-powered coding assistants such as *GitHub Copilot* and *Claude Code*.

View Details Apply on SimplyHired

Marketing Operations Manager

Company: Ulta Beauty, Inc.

Location: Bolingbrook, IL

Posted Oct 08, 2025

This role, reporting to the Director, Marketing Operations, will be responsible for driving efficiencies across the team, driving forward new process creation,…

View Details Apply on SimplyHired
401(k) dental insurance disability insurance

Patient Care Technician - AP4 Med/Surg/Tele - Nights

Company: Endeavor Health

Location: Chicago, Illinois

Posted Oct 07, 2025

View Details Apply on healthecareers.com

Registered Nurse (RN) - Per Diem Days

Company: Rush Specialty Hospital

Location: Chicago, IL

Posted Oct 08, 2025

Initial and ongoing systematic patient assessment. Interpret assessment/diagnostic data including labs and telemetry. Compensation: $56 per hour.

View Details Apply on SimplyHired

Flex Security Officer - On-Call - $18.50/hr

Company: Sunstates Security

Location: Burr Ridge, IL

Posted Oct 07, 2025

The flex officer provides trained, competent support by working shifts which become open due to illness, call-offs, weather, vacation, or other causes.

View Details Apply on SimplyHired

BUSINESS DATA ANALYST(EXECUTIVE I)

Company: State of Illinois

Location: Chicago, IL

Posted Oct 07, 2025

The ideal candidate will be comfortable working with large data sets, command-line analysis, and design thinking. 3 paid personal business days per year.

View Details Apply on SimplyHired

Customer Service Representative

Company: Roto-Rooter Services Company

Location: Lombard, IL

Posted Oct 08, 2025

Data entry, including customer contact information and relevant details concerning their plumbing problems. Be a trusted informational resource for Roto-Rooter…

View Details Apply on SimplyHired

Frequently Asked Questions

What are typical salary ranges for PTO roles by seniority?
Entry‑level PTO Analyst salaries range from $55,000 to $70,000 annually, mid‑level analysts earn $70,000 to $90,000, and senior PTO Program Managers or HRIS specialists command $90,000 to $120,000 plus bonus potential.
What skills and certifications are required for PTO positions?
Core skills include proficiency with HRIS platforms (Workday, SAP SuccessFactors, BambooHR), data analysis in Excel or Power BI, and regulatory knowledge of FMLA, ADA, and state leave laws. Certifications such as Certified Compensation Professional (CCP), HR Certification Institute (HRCI) HR-CP, or Workday HCM Associate enhance credibility.
Can PTO roles work remotely?
Yes, many PTO analysts and program managers operate fully remote, especially in tech firms. Remote work is supported by cloud‑based HRIS, secure VPNs, and collaboration tools like Slack and Microsoft Teams. Some roles still require occasional on‑site visits for policy rollout.
What are common career progression paths in PTO?
A PTO analyst can advance to Senior PTO Analyst, then to PTO Program Manager, followed by Director of Employee Benefits or HR Director roles. Lateral moves into broader HR analytics or compensation strategy are also common.
What industry trends are shaping PTO work?
Trends include the adoption of unlimited PTO policies, AI‑driven leave prediction models, integration of PTO data with wellness initiatives, and increased regulatory scrutiny on equitable leave practices. Companies also use data analytics to demonstrate ROI on PTO policies.

Related Pages

All Paid Time Off Jobs 23,177 jobs All Jobs in Chicago, IL 101,241 jobs Paid Time Off in Remote 747,681 jobs Paid Time Off in Other US Location 650,481 jobs Paid Time Off in New York City, NY 172,809 jobs Paid Time Off in Multiple Locations 152,175 jobs Paid Time Off in USA 136,446 jobs Paid Time Off in Washington DC 105,405 jobs Travel in Chicago, IL 79,837 jobs Full Time in Chicago, IL 46,687 jobs Retirement Plan in Chicago, IL 43,124 jobs 401(K) in Chicago, IL 37,542 jobs Health Insurance in Chicago, IL 34,384 jobs Life Insurance in Chicago, IL 33,039 jobs