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.

Relationship Banker

Company: Bank of America

Location: Joliet, IL

Posted Jan 23, 2025

Bank of America is seeking a client-focused individual for a role in Joliet, IL. The position involves engaging clients in the lobby, educating them on self-service resources like mobile banking and ATM, and assisting with transactions. Key responsibilities include processing cash transactions, building client relationships, and connecting them to suitable financial solutions. The ideal candidate should be a self-starter with a strong work ethic, excellent communication skills, and the ability to learn and adapt to new technologies. A background in financial services and sales experience is preferred. The role offers a competitive salary, benefits, and opportunities for career growth.

Relationship Banker

Company: Merrill

Location: Vernon Hills, IL

Posted Jan 23, 2025

Bank of America is seeking a client-focused individual for a role in their financial center. The job involves engaging clients in the lobby, educating them on self-service resources like mobile banking, online banking, or ATM, and assisting with transactions. Key responsibilities include accurately processing cash transactions, building relationships with clients, and connecting them to suitable financial solutions. The ideal candidate should be a self-starter with a strong work ethic, excellent communication skills, and the ability to learn and adapt to new technologies. They should also be comfortable working weekends and extended hours as needed. The role offers a competitive salary, benefits, and opportunities for career growth.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T0837)

Company: Target

Location: Oak Park, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Guest Advocate role with a starting hourly rate of $16.75 USD. The position involves providing exceptional guest service, engaging with guests, and promoting Target's services and benefits. The role is dynamic, involving tasks like scanning, bagging, and maintaining a clean work area. Target values teamwork, communication, and a positive attitude. The job requires flexibility, attention to detail, and the ability to work in varying conditions.

Retail Sales Associate - Deer Park

Company: Gap Inc.

Location: Lake Zurich, IL

Posted Jan 23, 2025

Athleta, a certified B Corp, is seeking passionate individuals to join their team. The role involves providing excellent customer service, educating customers about products, and promoting brand loyalty. The company values inclusivity, collaboration, and personal growth. Benefits include a merchandise discount, competitive Paid Time Off, volunteer time, extensive 401(k) plan, and health insurance. Athleta is committed to diversity and inclusion, recently recognized by Forbes as one of the World's Best Employers and Best Employers for Diversity.

Technical Development Program, Sensory

Company: Diageo

Location: Plainfield, IL

Posted Jan 23, 2025

Diageo, a global leader in beverage alcohol, is seeking a Sensory Specialist for a 12-month contract starting July 2025. The role involves gaining industry sensory knowledge, supporting Diageo Sensory Team projects, preparing and implementing sensory tests, and conducting panelist accreditation and trainings. The ideal candidate should have a relevant degree, sensory experience, strong communication skills, and the ability to work independently. The position offers opportunities for interaction with senior management, individual coaching, and performance feedback.

Retail Sales Associate, Full Time - Dierbergs-Edwards

Company: Gap Inc.

Location: Edwardsville, IL

Posted Jan 23, 2025

Old Navy is a fashion retailer that aims to democratize style and make shopping enjoyable. Established in 1994, the company offers high-quality, affordable essentials for the whole family. The role involves providing excellent customer service, product expertise, and promoting brand loyalty. Employees are expected to be good communicators, problem solvers, and able to handle customer interactions professionally. Benefits include a merchandise discount, competitive Paid Time Off, extensive 401(k) plan, and health insurance. Old Navy is committed to diversity and inclusion, recently recognized by Forbes as one of the World's Best Employers and Best Employers for Diversity.

Veterinarian

Company: Banfield Pet Hospital

Location: Chicago, IL

Posted Jan 23, 2025

General Manager - Rivertree Court

Company: Gap Inc.

Location: Vernon Hills, IL

Posted Jan 23, 2025

Old Navy is a fashion brand that aims to democratize style and make shopping enjoyable. Established in 1994, it offers high-quality, affordable essentials for the whole family. The company culture is community-oriented, fostering authenticity and high performance. The role involves leading a team, driving sales, and providing exceptional customer service. Benefits include a merchandise discount, competitive PTO, volunteer time, extensive 401(k), health insurance, and more. Old Navy is committed to diversity and inclusion, recently recognized by Forbes as one of the World's Best Employers and for Diversity.

Retail Sales Associate - Shops At Fox River

Company: Gap Inc.

Location: McHenry, IL

Posted Jan 23, 2025

Old Navy is a fashion retailer that aims to democratize style and make shopping enjoyable. Established in 1994, the company offers high-quality, affordable essentials for the whole family. The role involves providing excellent customer service, product expertise, and promoting brand loyalty. Employees are expected to be good communicators, problem solvers, and able to handle customer interactions professionally. Benefits include a merchandise discount, competitive Paid Time Off, extensive 401(k) plan, and health insurance. Old Navy is committed to diversity and inclusion, recently recognized by Forbes as one of the World's Best Employers and Best Employers for Diversity.

Internal Strategy & Process Engineering - Process Improvement Manager

Company: JPMorgan Chase

Location: Elgin, IL

Posted Jan 23, 2025

The Process Engineering Center of Excellence (PE COE) is a global team dedicated to driving business transformations and enhancing Chase Consumer & Community Banking's operational excellence. As a Process Improvement Manager, you'll lead consultant teams in strategic improvement efforts, delivering recommendations and execution support to realize business improvement targets. The role requires strong communication skills, leadership abilities, and experience in strategy, process improvement, or re-engineering. Preferred qualifications include process improvement experience, awareness of Lean Six Sigma, Agile methodologies, and project management skills.

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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