Paid Time Off Jobs in Chicago, IL

Positions 72,513 Updated daily

Paid Time Off demand in Chicago, IL is rising as tech firms prioritize work‑life balance to attract top talent.

Companies like Coinbase, Google, and local startups list explicit Paid Time Off hours, matching average Chicago, IL salary ranges that exceed the national median.

Salary transparency for Paid Time Off roles in Chicago, IL shows median compensation of $110K, with bonuses tied to project milestones.

Candidates can benchmark against Chicago, IL market data to negotiate higher Paid Time Off allowances and total compensation.

Software Engineer

Company: Morningstar

Location: Chicago, IL

Posted Oct 22, 2025

Lead or contribute to technical architecture discussions and design reviews. Own the full development lifecycle—from design and implementation to deployment and…

Billing Customer Service Specialist

Company: Banner Personnel Services, Inc.

Location: Chicago, IL

Posted Oct 21, 2025

Must be able to complete projects within the time allowed, be meticulous, be able to multitask, handle customer service inquiries both in person and by phone,…

Transportation Account Analyst (Onsite; LTL exp. req. $70-80K)

Company: #twiceasnice Recruiting

Location: Chicago, IL

Posted Oct 22, 2025

Streamline existing reporting and develop additional metrics. Maintain a detailed analysis of data. LTL data analysis : 1 year (Required).

Track Laborer

Company: CPKC

Location: Bensenville, IL

Posted Oct 22, 2025

Driver’s license verification and driving history. As a member of the Engineering team, a Track Laborer in the railroad industry plays a vital role in the…

Graphic Designer, Part Time

Company: PAWS Chicago

Location: Chicago, IL

Posted Oct 21, 2025

Manual dexterity to operate standard office equipment (e.g., computer keyboard, mouse, telephone, copier, printer).

Director of Service & Brand Alignment

Company: Encore Global

Location: Schiller Park, IL

Posted Oct 22, 2025

Brand Integration: Serve as primary Encore authority on Hilton service performance, embedding key principles from Hilton’s training philosophy into our own…

Project Manager

Company: Luma Health

Location: Chicago, IL

Posted Oct 22, 2025

Bachelor's Degree or related field. Serve as the project owner and main customer liaison throughout the implementation process, ensuring clear communication and…

Unarmed Security Officers

Company: St. Moritz Security Services

Location: Chicago, IL

Posted Oct 21, 2025

Valid driver's license (preferred). Responsible for site-specific duties and tasks based on assignment, which may include customer service, loss prevention,…

Golf Course Security Officer

Company: St. Moritz Security Services

Location: Chicago, IL

Posted Oct 21, 2025

PERC Card: Ability to obtain a valid Permanent Employee Registration Card (PERC). The primary responsibility of this position is to assist with the safety and…

Copywriter

Company: Caterpillar

Location: Chicago, IL

Posted Oct 22, 2025

Degree in a relevant field and experience in a creative role within an agency or in-house corporate environment or equivalent working experience.

Project Manager - HR (Hybrid)

Company: United Airlines

Location: Chicago, IL

Posted Oct 22, 2025

Program design and implementation skills required. Measure project performance using appropriate tools and techniques in order to monitor the progress of the…

DEVOPS ENGINEER

Company: Palco

Location: Chicago, IL

Posted Oct 22, 2025

Bachelor’s degree in computer science, computer engineering, or similar technical discipline. Excellent communication skills and ability to collaborate with…

Frequently Asked Questions

How do I find Paid Time Off jobs in Chicago, IL with clear salary details?
Search Job Transparency’s Paid Time Off category, filter by Chicago, IL, and review the salary field that lists base pay and PTO in dollars.
What salary range should I expect for Paid Time Off positions in Chicago, IL?
Typical Paid Time Off roles in Chicago, IL range from $90K to $130K, with PTO value included in the total compensation package.
Can I negotiate extra Paid Time Off in Chicago, IL after reviewing salary transparency?
Yes, use the disclosed salary and PTO data on Job Transparency to justify requests for additional days, especially in Chicago, IL where companies offer flexible policies.

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