Flexible Work Schedule Jobs in Chicago, IL

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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.

Sales Professional

Company:

Location: Oak Park, IL

Posted Jan 23, 2025

Transportation Security Officer

Company:

Location: DeKalb, IL

Posted Jan 23, 2025

Senior Manager - Aircraft Cybersecurity Operations

Company:

Location: Chicago, IL

Posted Jan 23, 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.

Part Time Security Supervisor

Company:

Location: Champaign, IL

Posted Jan 23, 2025

Securitas is hiring a Part Time Late Night Security Supervisor in Champaign, IL, offering a pay of $22.00/hour. The role involves training security officers, assisting with payroll, ensuring adequate coverage, preparing reports, and inspecting posts. The position requires a high school diploma, basic computer skills, security operations knowledge, high results orientation, strong interpersonal skills, and prior security or supervisor experience. Benefits include medical, dental, vision, life insurance, 401K options, paid time off, and more. Securitas values integrity, vigilance, and helpfulness, aiming to protect clients' assets and people.

Senior Developer - Information Technology

Company:

Location: Chicago, IL

Posted Jan 23, 2025

United Airlines is currently offering an exciting opportunity for a Senior Software Developer in a hybrid role based in Chicago. The successful candidate will be 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. United Airlines values diversity and inclusion, and this role is part of the united.com payments team, supporting different forms of payments. 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.

Senior Manager - Aircraft Cybersecurity

Company:

Location: Park Ridge, IL

Posted Jan 23, 2025

RETAIL SALES ASSOCIATE

Company:

Location: Oak Lawn, IL

Posted Jan 23, 2025

Ashley HomeStore is currently hiring Retail Sales Associates. The role involves selling furniture, mattresses, and home decor through excellent customer service. No prior sales experience is necessary, but it's a plus. Top writers can earn over $100,000. The compensation is based on written sales commission with a guaranteed hourly wage, potentially earning up to $100,000 or more. Benefits include generous paid time off, medical, dental, vision, and retirement benefits, and employee purchase discounts. Key responsibilities include assisting customers, demonstrating closing skills, and maintaining a clean working environment. Required skills include basic computer skills, strong communication, and organizational skills. Minimum 6 months of verifiable sales experience is preferred, and bilingual skills are a plus.

Senior Manager - Aircraft Cybersecurity

Company:

Location: Oakbrook, IL

Posted Jan 23, 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.

Restaurant Manager - Team Lead

Company:

Location: Mount Vernon, IL

Posted Jan 23, 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 23, 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.

Multi Site Security Officer

Company:

Location: Joliet, IL

Posted Jan 23, 2025

Securitas is hiring a Multi Site Security Officer in Joliet, IL, offering a comprehensive benefits package, weekly pay, and opportunities for career growth. The role involves monitoring and patrolling various client sites, enforcing regulations, and providing customer service. Ideal candidates should have at least 2 years of security experience, strong customer service skills, and be available to work any shift, including weekends and holidays. Securitas values Integrity, Vigilance, and Helpfulness, and offers a range of benefits including insurance, paid time off, and a referral program.

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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