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.

Lead Preschool Teacher

Company: St. Thomas The Apostle School

Location: Chicago, IL

Posted Apr 28, 2025

The ideal candidate will have a strong background in Active Playful Learning, 21st Century learning and a student centered philosophy.

View Details Apply on SimplyHired

Lead Software Engineer (C++ AND Golang) On-site, Chicago, IL or Reston, VA

Company: Comcast Corporation

Location: Chicago, IL

Posted Apr 29, 2025

Oversees the researching, writing and editing of documentation and technical requirements, including software designs, evaluation plans, test results, technical…

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health system full time be or bc

Northwestern Medicine Epileptologists Opportunities in the Chicago Metro Area

Company: Northwestern Medicine Regional Medical Group

Location: Orland Park, IL – Winfield, IL

Posted Apr 28, 2025

View Details Apply on healthecareers.com

CNC Swiss Set Up/Operator

Company: Precision-Tek Mfg., Inc

Location: Arlington Heights, IL

Posted Apr 29, 2025

Ability to read technical drawings and blueprints effectively. Operate CNC machines and equipment to manufacture parts as per technical drawings and…

View Details Apply on SimplyHired

Chef de Cuisine

Company: The Oakville Grill & Cellar

Location: Chicago, IL

Posted Apr 29, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

View Details Apply on SimplyHired

Sous Chef

Company: The Oakville Grill & Cellar

Location: Chicago, IL

Posted Apr 29, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

View Details Apply on SimplyHired
relocation assistance staffing agency contract

Travel CT Technologist - $2,652 per week

Company: Focus Staff

Location: Chicago, Illinois

Posted Apr 29, 2025

View Details Apply on healthecareers.com

HVAC Technician

Company: Topline HVAC

Location: Skokie, IL

Posted Apr 29, 2025

You will install, service, and repair heating and air conditioning systems. Familiarity with HVAC wiring diagrams. Respond to emergency maintenance requests.

View Details Apply on SimplyHired

Data Control Officer | Security (Access Control)

Company: Sitemetric

Location: Elk Grove Village, IL

Posted Apr 28, 2025

Sitemetric provides construction owners, general contractors, subcontractors, and workers data, hardware, software, and tech-enabled services in combinations…

View Details Apply on SimplyHired

Executive Sous Chef

Company: The Oakville Grill & Cellar

Location: Chicago, IL

Posted Apr 29, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

View Details Apply on SimplyHired

HVAC/R Service Technician - Light Commercial

Company: CoolSys

Location: Chicago, IL

Posted Apr 30, 2025

Sr, senior, Service Tech, refridgeration, HVAC, refrigeration, HVAC-R, HVAC/R, diagnostic, commercial, service, install, mechanical, mechanic, apprentice, AC,…

View Details Apply on SimplyHired

HVAC/R Service Technician - Light Commercial

Company: CoolSys

Location: Oak Lawn, IL

Posted Apr 30, 2025

Sr, senior, Service Tech, refridgeration, HVAC, refrigeration, HVAC-R, HVAC/R, diagnostic, commercial, service, install, mechanical, mechanic, apprentice, AC,…

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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