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.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: Bolingbrook, IL

Posted Jan 23, 2025

SAS Retail Services is seeking a Reset Merchandiser. The role involves ensuring the latest products match the new plan, offering flexibility with Monday - Friday work, and opportunities for growth. The job pays $15.80 per hour, provides paid training, and offers benefits including medical, dental, and life insurance. The ideal candidate is over 18, has reliable transportation, and can lift up to 25lbs.

Restaurant Manager

Company:

Location: Champaign, 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.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: Arlington Heights, IL

Posted Jan 23, 2025

SAS Retail Services is seeking a Reset Merchandiser. The role involves ensuring the latest products match the new plan, offering flexibility with Monday - Friday work, and opportunities for growth. The job pays $16.00 per hour, provides paid training, and offers benefits including medical, dental, and life insurance. The ideal candidate is over 18, has reliable transportation, and can lift up to 25lbs.

RETAIL SALES ASSOCIATE

Company:

Location: Rockford, IL

Posted Jan 23, 2025

Senior Developer - Information Technology

Company:

Location: Wilmette, IL

Posted Jan 23, 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.

Retail Sales Merchandiser

Company:

Location: Macomb, IL

Posted Jan 23, 2025

The text is a job posting for a Retail Sales position. The company is hiring for their Retail Sales team and is looking for candidates who are great at building relationships with store management, calling on customers, and managing their own territory. The ideal candidate should be looking to make $16.00 per hour, be 18 years or older, have some sales experience or willingness to learn, have a valid driver's license and a reliable vehicle, be able to lift up to 50 lbs, manage time efficiently, and work independently with little supervision.

SAS in Jewel – Part Time Retail Merchandiser

Company:

Location: Homewood, IL

Posted Jan 23, 2025

SAS Retail Services is seeking a Reset Merchandiser. The role involves ensuring the latest products match the new plan, offering flexibility with Monday - Friday work, and opportunities for growth. The job pays $16.00 per hour, provides paid training, and offers benefits including medical, dental, and life insurance. Candidates must be 18+, have reliable transportation, and a valid driver's license, capable of physical work involving moving, bending, and lifting up to 25lbs.

Rehab Nursing Tech I - C. N. A.

Company:

Location: Niles, IL

Posted Jan 23, 2025

Senior Manager - Aircraft Cybersecurity

Company:

Location: Orland Park, IL

Posted Jan 23, 2025

Furniture Sales Associate

Company:

Location: St. Charles, IL

Posted Jan 23, 2025

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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