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.

Night Maintenance

Company: Cracker Barrel

Location: Champaign, IL

Posted Jan 23, 2025

Cook

Company: Cracker Barrel

Location: Mattoon, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a Cook for their Effingham, IL location. The role involves preparing a variety of Southern dishes using the company's recipes and methods. The Cook will work in a team to ensure high standards of professional cooking, quality, safety, cleanliness, and hospitality. The position offers flexible hours, potential for promotion, and comprehensive training. Cracker Barrel emphasizes a culture of belonging, diversity, and inclusion, providing top-notch training, diverse career paths, and competitive pay and benefits. The company is committed to valuing all employees and fostering an environment where everyone feels accepted and celebrated.

Automation Technician

Company: Pactiv

Location: Hickory Hills, IL

Posted Jan 23, 2025

Category Manager - Bakery/Pastry

Company: Sysco

Location: Arlington Heights, IL

Posted Jan 23, 2025

Sysco is seeking a Category Manager for specialty/gourmet products. The role involves developing and executing category strategy, overseeing assortment, sourcing, pricing, promotions, sales training, and vendor relationships. Key responsibilities include assortment optimization, category/sales training, sourcing, pricing, vendor management, cross-functional collaboration, and technical skills like strong communication, computer proficiency, analytical skills, and business acumen. The ideal candidate should have a Bachelor's degree, 5+ years of experience in food service or consumer goods, and excellent negotiation skills.

Production Underwriter

Company: Argo Group

Location: Chicago, IL

Posted Jan 23, 2025

Retail Sales

Company: Cracker Barrel

Location: Ottawa, IL

Posted Jan 23, 2025

Target Security Specialist

Company: Target

Location: Chicago, IL

Posted Jan 23, 2025

Produce Associate

Company: Walmart

Location: Vernon Hills, IL

Posted Jan 23, 2025

This job posting is for a produce team member at Sam's Club. The role involves ensuring the availability, cleanliness, and freshness of produce, prioritizing member satisfaction, and providing excellent customer service. The ideal candidate should have experience with produce, be comfortable with change, and possess strong communication skills. Key responsibilities include maintaining a positive attitude, providing exceptional customer service, stocking merchandise, and maintaining inventory. The position offers competitive pay, benefits including health, financial, and time-off benefits, and opportunities for career growth. The minimum qualification is being 18 years old or above.

Winder Operator

Company: Pactiv

Location: Bourbonnais, IL

Posted Jan 23, 2025

Pactiv Evergreen Inc., a company formed by the merger of Pactiv LLC and Evergreen Packaging LLC, is prioritizing employee health and safety during the COVID-19 pandemic. They have implemented safety measures such as mandatory face coverings, daily screenings, social distancing, and hygiene protocols. The job involves setting up and operating winding machines, ensuring products meet quality standards, and maintaining a clean work area. Pactiv Evergreen offers career development, competitive wages, performance incentives, and a robust benefits package.

Dishwasher

Company: Cracker Barrel

Location: Mattoon, IL

Posted Jan 23, 2025

Creative Designer

Company: Accenture

Location: Chicago, IL

Posted Jan 23, 2025

Retail Sales

Company: Cracker Barrel

Location: Mount Vernon, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a Retail Sales team member for their Mount Vernon location. The role involves managing the retail shop, providing excellent guest service, and maintaining stock. The position offers flexible hours, potential for promotion, and comprehensive training. The company values diversity, equity, and inclusion, and provides a range of benefits including competitive pay, health benefits, and opportunities for career growth. The ideal candidate should be able to stand for long periods, lift up to 40 pounds, and work effectively with co-workers and managers.

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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