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.

Artificial Intelligence Tech Lead - Remote Work

Company: BairesDev

Location: Chicago, IL

Posted Jul 14, 2025

You'll establish and document best practices, transfer knowledge across teams, serve as a point of contact for upper management, and interact with key…

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Transporation Security Officer

Company: Department of Homeland Security - Transportation Security Administration

Location: Peoria, IL

Posted Jul 14, 2025

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Experienced Painter/Drywall Finisher

Company: RBE LLC

Location: Chicago, IL

Posted Jul 14, 2025

Valid driver's license preferred. Candidates must have own tools and be authorized to work in the USA. Candidates must have large scale multi-family renovation…

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Customer Service Representative

Company: Lawson Products

Location: Chicago, IL

Posted Jul 14, 2025

Responds to a minimum of 40 calls per day in an inbound call center. Possesses entry-level problem solving kills. High School Diploma or GED.

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Housekeeping Aid Supervisor

Company: Department of Veterans Affairs - Veterans Health Administration

Location: North Chicago, Illinois

Posted Jul 14, 2025

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Senior Accountant/Bookkeeper

Company: STANLEY ZILBER & ASSOCIATES, PC

Location: Chicago, IL

Posted Jul 14, 2025

We are seeking a detail-oriented and experienced Senior Accountant/Bookkeeper. The ideal candidate will possess a strong background in Construction Accounting…

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Chef Sous

Company: The Metropolitan

Location: Chicago, IL

Posted Jul 14, 2025

Organize and help in the service of all activities concerning ala carte, employee meals and private dining rooms. 2-3 years as line cook.

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Residential Lead Painter / Project Manager

Company: Classet

Location: Chicago, IL

Posted Jul 14, 2025

5+ years of management experience in a residential painting, construction, or drywall field. We offer customers everything they need in a painting contractor,…

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Copywriter HYBRID — FULL-TIMECHICAGO

Company: Edelman

Location: Chicago, IL

Posted Jul 14, 2025

High-level concepting, tactical program ideation and copywriting for a wide range of brand experiences, social content and marketing deliverables that generate…

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Accountant

Company: Corporate Leadership Center, NFP

Location: Chicago, IL

Posted Jul 14, 2025

Assist with the annual audit, including preparing supporting information, answering questions and reviewing annual reports and Form 990.

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CNC Machine Operator I-Second Shift

Company: Dynamic Manufacturing

Location: Hillside, IL

Posted Jul 14, 2025

Prolonged periods of sitting at a desk and working on a computer. The CNC Machine Operator is responsible for the manufacture of parts per plant.

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PRN Retail Pharmacist (Howard Brown CHC)

Company: Cardinal Health

Location: Chicago, IL

Posted Jul 14, 2025

Participates in supervision of technical staff. Immunization Certification or willing to become a certified immunizer within 90 days of hire.

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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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