Flexible Work Environment Jobs in Chicago, IL

76,048 open positions · Updated daily

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.

UI/UX Designer

Company: Velvetech

Location: Chicago, IL

Posted Feb 22, 2025

Proficiency in AI-driven design tools such as Figma with AI plugins, Adobe XD with Sensei features, or similar is required.

View Details Apply on SimplyHired

Experienced Residential Electrician

Company: Zanite Electrical

Location: Chicago, IL

Posted Feb 26, 2025

Valid driver’s license and clean driving record. Assembling, installing, testing, and maintaining electrical or electronic wiring, equipment, appliances,…

View Details Apply on SimplyHired
sign-on bonus contract professional growth

Cath Lab Technologist - $37-56 per hour

Company: Advocate Aurora Health

Location: Chicago, Illinois

Posted Feb 19, 2025

View Details Apply on healthecareers.com

Backend Software Engineer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Feb 21, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

View Details Apply on SimplyHired

Pharmacist-Drug Diversion Surveillance Analyst, Full-time Days

Company: Northwestern Medicine

Location: Chicago, IL

Posted Feb 20, 2025

We consider this on a case-by-case basis and follow all state and federal guidelines. We offer a wide range of benefits that provide employees with tools and…

View Details Apply on SimplyHired

Managing Associate Teacher - Little Village

Company: Carole Robertson Center for Learning

Location: Chicago, IL

Posted Feb 27, 2025

Lead the collaboration with the TA, Aides, and Program Advisor team in the creation and facilitation of studies to support weekly lesson plans, including daily…

View Details Apply on SimplyHired

AI Training Physics - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Feb 21, 2025

You can work on your own schedule. You will measure the progress of these AI chatbots, evaluate their logic, and solve problems to improve the quality of each…

View Details Apply on SimplyHired

Senior Data Analyst

Company: Chicago Public Schools

Location: Chicago, IL

Posted Feb 24, 2025

Effectively communicate technical findings to both technical and non-technical audiences. Strong understanding of statistical concepts and data analysis…

View Details Apply on SimplyHired

Plumbing Service Technician

Company: Stellar Plumbing

Location: Elk Grove Village, IL

Posted Feb 24, 2025

Plumbing Service Technicians determine service needs, quote prices in the field and perform repairs. Must be willing to pursue, develop, and participate in…

View Details Apply on SimplyHired
escape the endless cycle of crippling debt forwardthinking rapidly growing organization reimagining our technology platform

Lead Software Engineer in Test

Company: Beyond Finance

Location: Chicago, IL

Posted Feb 25, 2025

Beyond Finance is a rapidly growing financial technology company committed to helping individuals escape debt. They are seeking a Lead Software Development Engineer in Test to join their team. The role involves working closely with the team to verify software quality, planning and building automation, and mentoring other team members. Beyond Finance offers a collaborative work environment, competitive benefits, and opportunities for career development.

View Details Apply on BuiltIn
contract travel health savings account

Local Contract Cath Lab Technologist - $59-67 per hour

Company: Host Healthcare

Location: Chicago, Illinois

Posted Feb 19, 2025

View Details Apply on healthecareers.com

Registered Nurse

Company: DAVITA

Location: Chicago, IL

Posted Feb 19, 2025

Comprehensive benefits: medical, dental, vision, 401k, paid time off, PTO cash out, DaVita-negotiated discounts on hundreds of items from your cell phone plan…

View Details Apply on SimplyHired

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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