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.

Server

Company: Cracker Barrel

Location: Gurnee, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store in Gurnee, IL is seeking a server who is friendly and guest-focused. The role involves serving customers in a fast-paced, family-friendly environment, with flexible hours and no tip sharing. The company emphasizes a culture of belonging, diversity, and inclusion, offering top-notch training, diverse career paths, and competitive benefits including weekly pay, health benefits, and a 401K plan. The job description also highlights the company's commitment to equality and its stance against racism.

Senior Software Engineer (Java)

Company: Adyen

Location: Chicago, IL

Posted Jan 23, 2025

MGR - Engineering Manager - JAVA - (Ideally CHI but can be REMOTE)

Company: Addison Group

Location: Chicago, IL

Posted Jan 23, 2025

The job posting is for an Engineering Manager position in Chicago, IL. The ideal candidate should have hands-on technical leadership and people management experience, proven development experience in a modern technology stack, and a passion for building creative, scalable solutions to complex problems. The company uses a variety of technologies including Spring Boot, Java, Kotlin, TypeScript, Angular, Webpack, Sass, Neo4j, Redis, RabbitMQ, JUnit, Jasmine, Karma, Protractor, Selenium, AWS, Ansible, Terraform, Hashicorp, Docker, Jira, Slack, Gitlab, and G Suite.

SAP Tech Arch Consultant (Hybrid Arch)

Company: Accenture

Location: Chicago, IL

Posted Jan 23, 2025

Accenture's SAP practice is highlighted, emphasizing their expertise in design thinking, agile methodologies, and cutting-edge technologies like IoT, automation, and AI. They've developed myConcerto, a blend of SAP and Accenture, aiding clients in achieving significant victories. Accenture invests in training employees on new SAP technologies such as SAP Leonardo, S/4HANA, and Cloud, supported by a vast community of over 50,000 members. Their achievements are recognized with over 70 SAP awards, making them the leading partner for SAP SuccessFactors, SAP Ariba, SAP Hybris, SAP FieldGlass, and SAP Concur. The job role involves being an SAP Cloud expert, providing technical support for cloud migrations, administering SAP on Cloud, defining data migration strategies, and analyzing cloud performance. Minimum requirements include 3 years of SAP Cloud and Basis experience, 2 years of Linux OS experience, and at least one Cloud certification. Bonus points for SAP S/4, SAP PO, and SAP Security certifications.

Customer Specialist In Training - Part Time

Company: CarMax

Location: O'Fallon, IL

Posted Jan 23, 2025

CarMax is seeking a Customer Specialist for their O'Fallon, Illinois location. The role involves providing exceptional customer service, guiding customers through the buying and selling process, conducting vehicle condition assessments, and performing various administrative duties. The ideal candidate will have strong communication skills, the ability to build and maintain relationships, and a high level of integrity. No specific degree is required, but sales and customer service experience is preferred. CarMax is recognized as a great place to work, offering opportunities for career growth and commitment to diversity and training.

Full-Time Assistant Manager

Company: Cinemark

Location: Rock Island, IL

Posted Jan 23, 2025

Cinemark is currently hiring for Assistant Manager positions, offering a range of benefits including a discount, 401k, growth opportunities, education assistance, health benefits, parental leave, and paid time off. The role involves assisting in theatre operations, training staff, ensuring adherence to policies, and maintaining cleanliness and safety. The position is often temporary or training-based, with potential for promotion after six months and completion of the Management Accreditation Program. Essential duties include following GM's direction, training staff, preparing reports, inspecting theatre property, and ensuring superior customer service. Requirements include being at least 18, having a high school diploma or equivalent, completing Cinemark's management courses, food handling training, and passing background checks. Physical demands include frequent lifting, standing, and reaching.

Retail Sales

Company: Cracker Barrel

Location: Rock Island, IL

Posted Jan 23, 2025

To-Go Hospitality

Company: Cracker Barrel

Location: Mattoon, IL

Posted Jan 23, 2025

Cracker Barrel Old Country Store is seeking a To-Go Specialist in Effingham, IL. The role involves supporting the catering and to-go side of the business, ensuring guests can enjoy their homestyle favorites on-the-go. Responsibilities include taking detailed orders, swiftly packing meals, and maintaining a clean and well-stocked To-Go area. The position offers growth opportunities, great benefits, and a culture of hospitality. It's a tipped role with no tipping-out required. Cracker Barrel emphasizes inclusivity and equality, with a zero-tolerance policy for racism.

Financial Team Admin

Company: Addison Group

Location: Chicago, IL

Posted Jan 23, 2025

SAP Fiori Consultant

Company: Accenture

Location: Chicago, 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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