Flexible Work Schedule Jobs in Chicago, IL

75,597 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.

Transporation Security Officer

Company: Department of Homeland Security - Transportation Security Administration

Location: Peoria, IL

Posted Jul 14, 2025

View Details Apply on usajobs.gov

RN REGISTERED NURSES

Company: Park View

Location: Chicago, IL

Posted Jul 14, 2025

Current, unencumbered state license to practice as a Registered Nurse. Will direct the day-to-day functions of the nursing assistants in accordance with current…

View Details Apply on SimplyHired

Physician (Staff Pathologist)

Company: Department of Veterans Affairs - Veterans Health Administration

Location: Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on usajobs.gov

Door Host/Security Staff - Late Nights, Evenings

Company: Gus' Sip & Dip (1262)

Location: Chicago, IL

Posted Jul 13, 2025

Door Host/Security Staff are responsible for the initial, warm greeting of guests and for maintaining the safety of guests and employees, carding guests,…

View Details Apply on SimplyHired

Housekeeping Aid Supervisor

Company: Department of Veterans Affairs - Veterans Health Administration

Location: North Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on usajobs.gov

Psychiatrist

Company: Department of Veterans Affairs - Veterans Health Administration

Location: North Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on usajobs.gov

RN REGISTERED NURSES

Company: Center Home for Hispanic Elderly

Location: Chicago, IL

Posted Jul 14, 2025

Current, unencumbered state license to practice as a Registered Nurse. Will direct the day-to-day functions of the nursing assistants in accordance with current…

View Details Apply on SimplyHired

Residential Lead Painter / Project Manager

Company: Classet

Location: Chicago, IL

Posted Jul 14, 2025

5+ years of management experience in a residential painting, construction, or drywall field. We offer customers everything they need in a painting contractor,…

View Details Apply on SimplyHired

Supervisory Information Technology Specialist (Policy and Planning)

Company: Department of the Army - U.S. Military Entrance Processing Command

Location: North Chicago, Illinois

Posted Jul 13, 2025

View Details Apply on usajobs.gov

Registered Nurse- FT/PT PM Shift Only!

Company: Pearl of Montclare

Location: Elmwood Park, IL

Posted Jul 14, 2025

Prepare & administer medications as ordered by the physician. Admit, transfer and discharge residents as required. Join The Pearl of Montclare!

View Details Apply on SimplyHired
relocation assistance full time be or bc

Gastroenterologist Opportunity – Established Group in Chicago

Company: RosmanSearch

Location: Chicago, Illinois

Posted Jul 14, 2025

View Details Apply on healthecareers.com

Associate Manager, Investment, Search

Company: Rise

Location: Chicago, IL

Posted Jul 14, 2025

Collaborate with leadership and peers to develop solutions that will enhance our operational efficiency, tools, and systems, and improve current workflows.

View Details Apply on SimplyHired

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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