Flexible Work Environment Jobs in Chicago, IL

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Looking for Flexible Work Environment jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Work Environment 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…

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.

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…

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.

Frequently Asked Questions

What are typical salary ranges by seniority in flexible work roles?
Entry‑level (0‑2 yrs) typically earns $70k–$90k. Mid‑level (3‑5 yrs) ranges $90k–$120k. Senior (6‑10 yrs) $120k–$160k. Staff/Principal engineers $160k–$200k. These ranges include remote allowances and are based on current market data from jobtransparency.com.
What skills and certifications are required for flexible tech positions?
Essential skills include JavaScript (React, Node.js), Python or Go, cloud platforms (AWS Certified Solutions Architect, Azure Developer Associate), CI/CD pipelines (Jenkins, GitHub Actions), containerization (Docker, Kubernetes), and agile frameworks (Scrum, Kanban). Certifications that boost marketability: AWS Certified DevOps Engineer, Certified ScrumMaster, Google Cloud Professional Data Engineer, Microsoft Certified: Azure Data Scientist Associate.
Is remote work available for most flexible roles?
Yes—over 90% of positions are fully remote with optional hybrid options. Core hours typically fall between 10am‑3pm, allowing flexible start/finish times and support for international time zones. Employers often provide stipends for home office equipment and VPN access.
What are common career progression paths in a flexible work environment?
Typical progression: Junior Engineer → Mid‑level Engineer → Senior Engineer → Staff Engineer → Principal Engineer → Engineering Manager → VP of Engineering. Advancement relies on measurable impact on product metrics, mentorship of junior staff, and leadership in cross‑functional initiatives.
What industry trends are shaping flexible work roles?
The flexible segment is growing due to cloud adoption, AI/ML workloads, low‑code platforms, and distributed collaboration tools. Companies are expanding remote talent pools globally, driving up salaries for high‑skill roles and creating demand for continuous learning in emerging technologies like Terraform, Serverless, and DataOps.

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