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.

Grinder/Machine Operator

Company: Tool Steel Service

Location: Bridgeview, IL

Posted Aug 15, 2025

Light computer entry for processing orders. Machine Operators: run machines (grinding, sawing, milling equipment) to process steel products to meet customer…

Plumber II

Company: Insight

Location: Chicago, IL

Posted Aug 15, 2025

This position is expected to work across trade disciplines to and including but not limited to the following; repair and maintenance of mechanical and…

Truck Driver CDL A Home Daily

Company: Ryder

Location: Chicago, IL

Posted Aug 15, 2025

Ensuring compliance with applicable federal and/or state laws, regulations, and/or agency rules, standards and guidelines. Ryder Drivers are Paid Weekly.

Utilization Reviewer PRN-Behavioral Health Services

Company: Northwestern Medicine

Location: Chicago, IL

Posted Aug 15, 2025

Responsible for utilization review calls within BHS, including precertification, continued stay review, discharge reviews, and retrospective reviews and appeals…

Electrician

Company: Tradesmen International, Inc.

Location: Chicago, IL

Posted Aug 15, 2025

Active Michigan Journeyman Electrician license. Ability to read and interpret electrical drawings and plans. Install electrical fixtures and related components.

Armed Security Officer/Driver

Company: Kates Detective Agency

Location: Chicago, IL

Posted Aug 15, 2025

Remain in compliance with local, state, and federal regulations. This position involves patrolling client properties, ensuring safety, and driving company…

Pre-Kindergarten Long Term Substitute Teacher - 2025/2026 School Year (Donoghue Campus)

Company: University of Chicago Charter School

Location: Chicago, IL

Posted Aug 15, 2025

Applicant should have a Bachelor’s degree in education and state certification; at least 2 years of urban teaching experience in related field; and proven…

Building Service Supervisor

Company: University of Illinois

Location: Chicago, IL

Posted Aug 15, 2025

Supervise operations and activities of all custodial personnel engaged in cleaning and maintaining campus housing facilities for residents, guests and…

Pro Sales Associate - Chicago Metro

Company: Behr Paint Company

Location: Chicago, IL

Posted Aug 15, 2025

When an outside rep sends a contractor to you for paint, you will roll out the red carpet by collaborating with them to get exactly the right products for their…

Junior Sushi Chef

Company: Grain + Sea

Location: Chicago, IL

Posted Aug 15, 2025

Grain + Sea* is a modern, buffet-style sushi restaurant where guests build their perfect sushi box and pay by weight. Free staff meal during shift.

Presentation Designer

Company: Rise

Location: Chicago, IL

Posted Aug 15, 2025

0–2 years of professional experience in visual design, presentation design, or a related creative field. You’ll work closely with strategists, planners, and…

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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