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.

Maintenance Electrician (3rd Shift | $41.36/hr | Union | Direct Hire | Chicago, IL)

Company: Assist Staffing

Location: Chicago, IL

Posted Aug 17, 2025

Read and interpret electrical schematics and technical manuals. Minimum 3+ years’ experience in industrial maintenance with a strong electrical focus.

CNC Lathe Operator (2nd Shift)

Company: ERA Industries LLC

Location: Elk Grove Village, IL

Posted Aug 17, 2025

Ability to use basic measuring tools (Micrometer, Caliper, Thread Gages, Pin Gages, Bore Gages, Dial Indicators, Height Gages). Assist with machine set up.

On Call Hospice RN

Company: Oasis Hospice & Palliative Care, Inc.

Location: Chicago, IL

Posted Aug 18, 2025

Must be a licensed driver with an automobile that is insured in accordance with state of Illinois requirements and is in good working order.

Accounting Supervisor - Chicago IL, Loop

Company: Savant Wealth Management

Location: Chicago, IL

Posted Aug 18, 2025

*Lead with purpose:* Coach, develop, and empower a team of accountants, setting clear goals and aligning their efforts to Savant’s mission and strategic…

Class A CDL Owner Operator

Company: Trucking Edge

Location: Chicago, IL

Posted Aug 18, 2025

Earn 75% of line haul utilizing own trailer. 100% of billed fuel surcharge along with 100% of accessorials. Earn 70% of line haul revenue.

Private Equity Tech Sales - Founding Team Member for AI Startup

Company: Nestbox AI

Location: Chicago, IL

Posted Aug 18, 2025

*Founder-Level Impact:* You’ll be the first sales hire, working directly with our technical founders to shape GTM strategy, refine our offering for PE, and have…

Senior Manager - Global Payment Network Information Security Office (ISO) Consultant

Company: Capital One

Location: Chicago, IL

Posted Aug 18, 2025

Collaborating with enterprise cyber teams and tech architects in defining and driving the cyber architecture strategy and guiding principles for the…

Registered Nurse Hospice Case Manager - Flexible Schedule

Company: LifeChoice Hospice and Palliative Care

Location: Mount Prospect, IL

Posted Aug 18, 2025

Current RN license in IL. Perform and document patient evaluations, visits, and care in compliance with federal, state, and accreditation standards.

Unarmed Security Officer ( North/West Suburbs)

Company: American Public Defense Inc.

Location: Chicago, IL

Posted Aug 17, 2025

Valid driver's license/state ID. Logging in vendors and visitors. Maintain safety and security of property. Complete daily logs and incident reports.

Senior Manager - Global Payment Network Information Security Office (ISO) Consultant

Company: Capital One

Location: Chicago, IL

Posted Aug 18, 2025

Collaborating with enterprise cyber teams and tech architects in defining and driving the cyber architecture strategy and guiding principles for the…

Customer Experience Supervisor

Company: TJ Maxx

Location: Oak Brook, IL

Posted Aug 17, 2025

Benefits include: Associate discount; EAP; smoking cessation; bereavement; 401(k) Associate contributions; child care & cell phone discounts; pet & legal…

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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