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.

Store Associate

Company: CVS Health

Location: Chicago, IL

Posted Jan 24, 2025

CVS Health is seeking Retail Store Associates to join their team, emphasizing a human-centric approach to healthcare. The role involves providing excellent customer service, maintaining the sales floor, supporting store activities, and assisting in the pharmacy. The company offers competitive pay, comprehensive benefits, and opportunities for career growth. No prior retail experience is required, but a high school diploma is preferred.

Director, Branch Network - East

Company: Grainger

Location: Lake Forest, IL

Posted Jan 24, 2025

Assistant Store Leader

Company: Kroger

Location: Carbondale, IL

Posted Jan 24, 2025

Corporate Event Planner - Financial Services Events

Company: TransUnion

Location: Chicago, IL

Posted Jan 24, 2025

TransUnion is seeking a Corporate Event Planner with 5-7 years of experience in event execution, including both proprietary and third-party events. The role involves managing all logistics, production, and budget for advisory board meetings, proprietary forums, and tradeshows. The ideal candidate should have strong project management skills, understand event technologies, and be able to work in a fast-paced environment. The position offers a competitive salary range of $72,300.00 - $105,000.00 annually, along with comprehensive benefits and a commitment to diversity and inclusion.

Service and Engagement Team Leader

Company: Target

Location: Joliet, IL

Posted Jan 24, 2025

Target is offering a competitive pay range of $23.75 - $40.40 per hour, with additional benefits such as health insurance, 401(k), employee discount, and paid time off. The role of a Service and Engagement Team Leader involves guest service, team management, and business operations. Target values diversity, equity, and inclusion, and provides opportunities for career growth. The job requires strong communication, leadership, and problem-solving skills, with a flexible schedule including weekends and holidays.

Health & Benefits - Support Specialist Team Lead (Remote)

Company: Inspira Financial

Location: Chicago, IL

Posted Jan 24, 2025

Inspira Financial is seeking a Team Lead Support Specialist to guide, support, and mentor Support Specialists. The role involves coaching, training, and developing team members, assisting with policy and procedure updates, and testing new product offerings and software applications. The ideal candidate should have strong communication skills, be action-oriented, and possess a high level of composure. Inspira Financial is recognized for its remarkable growth and outstanding workplace culture, offering competitive compensation and benefits.

FUEL CENTER/CLERK

Company: Kroger

Location: Springfield, IL

Posted Jan 24, 2025

Client Documentation

Company: JPMorgan Chase

Location: Chicago, IL

Posted Jan 24, 2025

JPMorgan Chase is seeking a Client Documentation Associate for the Commercial & Investment Bank's Client Onboarding team. The role involves working with clients, internal teams, and partners to ensure all necessary documentation is ready for new or updated client accounts. Responsibilities include managing the account opening and client documentation workflow, conducting research for product setup and account opening, ensuring documentation adheres to bank policies, and demonstrating problem-solving skills. The ideal candidate should have 3+ years of relevant experience, excellent communication skills, and a Bachelor's degree. Preferred qualifications include a paralegal or Juris Doctor certificate and experience in financial services.

Assistant Store Manager

Company: Kohl's

Location: O'Fallon, IL

Posted Jan 24, 2025

Lead Software Engineer-0156

Company: Inspira Financial

Location: Chicago, IL

Posted Jan 24, 2025

Inspira Financial is seeking a Lead Software Engineer to join their team. The role involves the full software development life cycle, from conception to deployment. The ideal candidate should have relevant experience with frontend and backend coding languages, software development architecture, and design patterns. They should also have a strong technical background in DevOps and automation, and excellent communication skills. The company values diversity and offers a collaborative, fun environment that champions career development. Inspira Financial provides health, wealth, retirement, and benefits solutions, serving over 7 million clients with more than $62 billion in assets.

Frequently Asked Questions

What are typical salary ranges for Flexible Work Schedule roles at different seniority levels?
Entry‑level: $60‑$90k annually. Mid‑level: $90‑$140k. Senior: $140‑$200k. Lead/Director: $200‑$300k. These ranges vary by tech stack, region, and company size but generally reflect market rates for remote work.
What technical skills and certifications are most valuable for Flexible Work Schedule positions?
Key skills: proficiency with asynchronous tools (Slack, Zoom, Microsoft Teams), project management software (Jira, Asana, Trello), version control (Git/GitHub), cloud platforms (AWS, Azure, GCP), and CI/CD pipelines. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster (CSM), or PMP add credibility and open higher‑pay roles.
Are Flexible Work Schedule roles fully remote, or do they require occasional office visits?
Most Flexible Work Schedule listings allow 100% remote work, with optional hybrid or occasional on‑site meetings for team alignment. Employers typically provide a stipend for home‑office setup and stipulate flexible hours to accommodate different time zones.
How can a professional advance their career while working a Flexible Work Schedule?
Start as a junior engineer or analyst, then move to senior roles, team lead, or product owner. Remote experience can lead to global project assignments, mentorship positions, and eventually senior leadership roles such as Remote Program Manager or VP of Engineering with flexible terms.
What current industry trends are impacting Flexible Work Schedule opportunities?
The rise of AI‑driven collaboration tools (Figma’s auto‑layout, GitHub Copilot), increased focus on cybersecurity for remote teams, and the growth of virtual offices are shaping demand. Companies are prioritizing flexible schedules to retain high‑talent talent in a post‑pandemic world.

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