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.

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 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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