Flexible Schedule Jobs in Chicago, IL

34,503 open positions · Updated daily

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

Artificial Intelligence Tech Lead - Remote Work

Company: BairesDev

Location: Chicago, IL

Posted Jul 14, 2025

You'll establish and document best practices, transfer knowledge across teams, serve as a point of contact for upper management, and interact with key…

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Transporation Security Officer

Company: Department of Homeland Security - Transportation Security Administration

Location: Peoria, IL

Posted Jul 14, 2025

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Field Supervisor

Company: Department of Commerce - U.S. Census Bureau

Location: Bureau County, IL

Posted Jul 13, 2025

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Physician (Staff Pathologist)

Company: Department of Veterans Affairs - Veterans Health Administration

Location: Chicago, Illinois

Posted Jul 14, 2025

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Construction Crew Lead

Company: ALFF CONSTRUCTION LLC

Location: Chicago, IL

Posted Jul 14, 2025

Have own tools for routine tasks. Strong hands-on skills in at least two trades: HVAC, refrigeration, plumbing, electrical, or carpentry.

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Psychiatrist

Company: Department of Veterans Affairs - Veterans Health Administration

Location: North Chicago, Illinois

Posted Jul 14, 2025

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Field Representative

Company: Department of Commerce - U.S. Census Bureau

Location: Kendall County, IL

Posted Jul 13, 2025

View Details Apply on usajobs.gov

Residential Lead Painter / Project Manager

Company: Classet

Location: Chicago, IL

Posted Jul 14, 2025

5+ years of management experience in a residential painting, construction, or drywall field. We offer customers everything they need in a painting contractor,…

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Accountant

Company: Corporate Leadership Center, NFP

Location: Chicago, IL

Posted Jul 14, 2025

Assist with the annual audit, including preparing supporting information, answering questions and reviewing annual reports and Form 990.

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PRN Retail Pharmacist (Howard Brown CHC)

Company: Cardinal Health

Location: Chicago, IL

Posted Jul 14, 2025

Participates in supervision of technical staff. Immunization Certification or willing to become a certified immunizer within 90 days of hire.

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relocation assistance full time be or bc

Gastroenterologist Opportunity – Established Group in Chicago

Company: RosmanSearch

Location: Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on healthecareers.com

Registered Nurse- FT/PT PM Shift Only!

Company: Pearl of Montclare

Location: Elmwood Park, IL

Posted Jul 14, 2025

Prepare & administer medications as ordered by the physician. Admit, transfer and discharge residents as required. Join The Pearl of Montclare!

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Frequently Asked Questions

What are typical salary ranges for Flexible Schedule roles by seniority?
Entry‑level positions pay $60k–$80k annually. Mid‑level engineers and data scientists earn $80k–$120k. Senior roles, including lead architects and senior product managers, range $120k–$180k, while executive‑level talent can command $180k–$250k with bonuses and equity.
What skills and certifications are required for a Flexible Schedule tech career?
Remote collaboration tools (Zoom, Slack) and version control (Git) are essentials. Technical stacks vary: developers need proficiency in JavaScript/TypeScript, Python, or Go; DevOps engineers should master AWS, Terraform, and Kubernetes; data scientists must be fluent in Python, R, SQL, and machine‑learning libraries. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster, or Google Cloud Professional Data Engineer boost credibility.
Is remote work a standard option for Flexible Schedule listings?
Yes—most Flexible Schedule roles are fully remote or offer a hybrid model. Companies provide cloud‑based development environments, VPN access, and asynchronous communication protocols, allowing you to work from any location while staying connected to distributed teams.
What career progression paths exist within Flexible Schedule roles?
Start as a junior engineer or analyst, then advance to senior, team lead, or principal engineer. Product managers move from associate to senior PM, then to director or VP of Product. Technical architects can transition to solutions architect or head of engineering, often with increased ownership of strategy and mentoring.
What industry trends are shaping Flexible Schedule job opportunities?
Hybrid work models are becoming standard, driven by AI‑powered scheduling tools that manage availability across time zones. Remote‑first startups and Fortune 500 firms alike offer flexible hours to attract global talent, boosting demand for digital nomads and professionals seeking work‑life balance.

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