Flexible Work Schedule Jobs in Chicago, IL

75,610 open positions · Updated daily

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

Senior Manager - Aircraft Cybersecurity

Company:

Location: Niles, IL

Posted Jan 22, 2025

United Airlines is inviting applications for a Senior Manager - Aircraft Cybersecurity Operations role. This position involves leading a team of cybersecurity engineers to ensure end-to-end security architecture of United's aircraft-related products. The role requires aviation experience, strong technical communication skills, and experience in risk management. United offers a competitive benefits package and values diverse experiences. The ideal candidate will have a Bachelor's degree in a STEM or Engineering field, 9+ years of related experience, and a proven ability to communicate technical concepts to non-technical audiences.

Rehab Nursing Tech I - C. N. A.

Company:

Location: Gurnee, IL

Posted Jan 22, 2025

Encompass Health Rehabilitation Institute of Libertyville is seeking a Rehab Nursing Technician I. The role involves providing direct patient care, assisting RNs or LPNs, and promoting patient satisfaction and outcomes. The position offers opportunities for career growth, including a dedicated RNT Career Framework program. Encompass Health, a national leader in post-acute care, fosters continuous learning and growth, and offers competitive compensation and benefits.

Restaurant Manager - Quarterly Bonus Available

Company:

Location: Gurnee, IL

Posted Jan 22, 2025

Chili's Managers are passionate about hospitality, connecting with team members and guests, and creating a fun work environment. They are responsible for ensuring a great guest experience, leading shifts, managing costs, and developing team members. Chili's values a culture of fun, teamwork, and accountability, with a focus on food perfection and inclusivity.

Chili's Grill & Bar, Restaurant Manager - Calumet City

Company:

Location: Calumet City, IL

Posted Jan 22, 2025

Chili's Managers are passionate about hospitality, connecting with team members and guests, and creating a fun work environment. They are responsible for ensuring a great guest experience, leading shifts, managing costs, and developing team members. Chili's values a culture of fun, teamwork, and accountability, with a focus on food perfection and inclusivity.

Senior Manager - Aircraft Cybersecurity

Company:

Location: Chicago, IL

Posted Jan 22, 2025

United Airlines is inviting applications for a Senior Manager - Aircraft Cybersecurity Operations role. This position involves leading a team of cybersecurity engineers to ensure end-to-end security architecture of United's aircraft-related products. The role requires aviation experience, strong technical communication skills, and experience in risk management. United offers a competitive benefits package and values diverse experiences. The ideal candidate will have a STEM or Engineering degree, 9+ years of related experience, and knowledge of aviation cybersecurity and IT security best practices.

Sales Consultant

Company:

Location: Cary, IL

Posted Jan 22, 2025

Mattress Firm is offering a Sleep Expert position with extensive customer-centric training, excellent career growth opportunities, and comprehensive benefits. The role involves creating a customer-focused environment, providing technical knowledge, driving sales, and maintaining customer relationships. Mattress Firm emphasizes its commitment to helping people sleep well to live well, investing in new associates' training and offering performance-based bonuses. The company values diversity and inclusion, and encourages diverse candidates to apply.

Senior Manager - Aircraft Cybersecurity Operations

Company:

Location: North Riverside, IL

Posted Jan 22, 2025

Senior Developer - Information Technology

Company:

Location: Homewood, IL

Posted Jan 22, 2025

United Airlines is currently experiencing a period of growth and innovation, aiming to become the best airline in history. They are seeking a Senior Software Developer for a hybrid role in Chicago, responsible for developing critical applications, working with a team of developers, and focusing on delivering cloud-based solutions. The role involves managing the full development life cycle, serving as a technical expert, and collaborating with various teams. The ideal candidate should have a Bachelor's degree in a relevant field, 5+ years of full-stack development experience, proficiency in React, Typescript, C#, Node.js, and AWS/cloud technologies, and a deep understanding of accessibility fundamentals.

Frequently Asked Questions

What are typical salary ranges for flexible work schedule roles at different seniority levels?
Entry‑level (0‑2 years) $60k–$80k; Mid‑level (2‑5 years) $80k–$120k; Senior (5‑10 years) $120k–$180k; Lead/Principal (10+ years) $180k–$250k. International remote roles may have adjusted ranges such as $40k–$60k in emerging markets, reflecting local cost of living while maintaining equity.
What key skills and certifications are required for flexible work schedule positions?
Technical: Proficiency in Git, Docker, Kubernetes, and cloud platforms (AWS Certified Solutions Architect, Google Cloud Professional Data Engineer, or Azure Solutions Architect). Agile and project tools: Jira, Confluence, and automated testing frameworks. Soft skills: asynchronous communication, cultural competence, self‑management, and time‑zone coordination. Certifications like Certified Scrum Master (CSM), ITIL Foundation, and PMP are highly regarded for product and project roles.
Is remote work always an option for flexible schedule roles?
Most flexible schedule positions offer 100% remote or hybrid arrangements, with occasional on‑site requirements for quarterly collaboration or training. Companies often specify the percentage of remote work (e.g., 80% remote, 20% on‑site) and provide stipends for home‑office equipment. Applicants can verify the remote policy in the job description or during the interview.
What career progression paths exist within flexible work schedule roles?
Typical paths include: Junior Engineer → Senior Engineer → Tech Lead → Principal Engineer → Engineering Manager; or Product Manager → Senior Product Manager → Director of Product → VP of Product. Lateral moves into architecture, security, or data science are common for professionals seeking broader impact while maintaining flexible arrangements.
What are the current industry trends affecting flexible work schedule jobs?
Key trends: growth of asynchronous communication tools (e.g., Loom, Notion), AI‑driven workflow automation (e.g., GitHub Copilot, ChatGPT for code review), distributed version control at scale, micro‑tasking platforms, flexible sprint lengths, well‑being metrics integration, and digital nomad visas supporting cross‑border talent. Companies are also investing in continuous learning portals and remote‑first hiring practices.

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