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.

Electrician Journeyman - 90108690 - Chicago

Company: Amtrak

Location: Chicago, IL

Posted Aug 06, 2025

Experience in electrical repairs, and testing advanced electrical/electronic systems and reading, drafting, and interpreting circuit diagrams, schematics, and…

JANITOR III (DEPARTMENT OF FACILITIES MANAGEMENT) - SEIU 73 - VARIOUS LOCATIONS

Company: Cook County Offices Under the President

Location: Chicago, IL

Posted Aug 06, 2025

Candidates who are contacted will be required to produce original required documents (e.g., current driver’s license, diploma, school transcript, certifications…

Residential Construction Foreman and Laborer

Company: Home by Molly Marino and CZ Construction Group

Location: La Grange, IL

Posted Aug 06, 2025

Reliable transportation and a valid driver’s license. Handle *light electrical and plumbing tasks* as needed. You’ll be expected to manage job sites, coordinate…

Facilities Maintenance Technician(WELDER)

Company: Central Transport

Location: Hillside, IL

Posted Aug 06, 2025

*Carpentry *– install floor tiles including ceramic and VCT, repair and hang metal/wood doors, masonry repairs, concrete repairs, drywall, and other trades.

Cleaning Technician / General Labor

Company: Stanley Steemer

Location: Chicago, IL

Posted Aug 06, 2025

Valid, US driver's license. These are field-based positions and require travel in and around the surrounding area. Power tools preferred, but will train.

Maintenance Electrician

Company: Ann & Robert H. Lurie Children’s Hospital of Chicago

Location: Chicago, IL

Posted Aug 06, 2025

Maintains a valid driver s license and safe driving record. Working knowledge of building and life safety codes with specific knowledge of city, state and…

Controls Specialist

Company: Clear Engineering Recruitment

Location: Chicago, IL

Posted Aug 06, 2025

Blueprint reading skills and comfort with field documentation. Own the Field: Perform preventative maintenance, repairs, and logic modifications across live…

Sales Engineering Director - Modern Infrastructure

Company: Arrow Electronics, Inc.

Location: Itasca, IL

Posted Aug 06, 2025

This team of SEMs and sales engineers provide technical expertise through sales calls, presentations, solution design, product and proof of concept…

Customer Brand Ambassador & Sales Associate

Company: Legacy Forward Solutions

Location: Elmhurst, IL

Posted Aug 06, 2025

Learn and maintain strong product knowledge to educate customers effectively. Execute brand promotions and in-store marketing strategies.

Experienced Commercial Painter

Company: Southwest Coating Services

Location: Chicago, IL

Posted Aug 06, 2025

Reliable vehicle, valid driver's license and proof of insurance. 401K matching after 6 months of employment. Wallcovering installation a plus, but not required.

Teacher (PreK-3)

Company: Chicago Public Schools

Location: Chicago, IL

Posted Aug 06, 2025

ESSENTIAL FUNCTIONS: Responsible for instructional planning, including, but not limited to, providing written lesson plans and preparation in accordance with…

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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