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.

PART TIME SALES ASSOCIATE

Company: Von Maur

Location: Glenview, IL

Posted Oct 12, 2025

Own the customer experience – greet people sincerely, be friendly and thank every customer. Ring POS transactions and key account information.

View Details Apply on SimplyHired
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General Urologist Needed in Chicago Suburbs (Naperville/Bolingbrook)

Company: Duly Health and Care

Location: Chicago Suburbs, IL

Posted Oct 12, 2025

View Details Apply on healthecareers.com

Senior HVAC Project Manager

Company: Admiral Heating & Ventilating

Location: Hillside, IL

Posted Oct 13, 2025

Work with field and others on the project team to maintain project tracking and reporting to insure work progress and budget compliance.

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Breast Imaging Radiologist

Company: Endeavor Health

Location: Chicago, Illinois

Posted Oct 12, 2025

View Details Apply on healthecareers.com

Senior Lead Data Engineer

Company: Capital One

Location: Chicago, IL

Posted Oct 13, 2025

Collaborate with and across Agile teams to design, develop, test, implement, and support technical solutions in full-stack development tools and technologies.

View Details Apply on SimplyHired

SALES ASSOCIATE

Company: Von Maur

Location: Glenview, IL

Posted Oct 12, 2025

Own the customer experience – greet people sincerely, be friendly and thank every customer. Ring POS transactions and key account information.

View Details Apply on SimplyHired

Work from Home Clinical Pharmacist

Company: Adecco

Location: Chicago, IL

Posted Oct 13, 2025

Serve as a clinical resource working from a computer, reviewing prior authorizations and receiving phone calls from prior authorization pharmacy technicians and…

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Handyman/Laborer, Tradesman, 1099 Contractor

Company: Tenth Group LLC

Location: Chicago, IL

Posted Oct 12, 2025

Skills in construction painting, tile laying, flooring installation, frame carpentry, door hanging, caulking, trim carpentry, and glass installation.

View Details Apply on SimplyHired

Azure Engineer Cloud Architect

Company: Robotics Technologies

Location: Chicago, IL

Posted Oct 11, 2025

Nor will ROBOTICS TECHNOLOGIES LLC require in a posting or otherwise U.S. citizenship or lawful permanent residency in the U.S. as a condition of employment…

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Construction Project Manager

Company: Arete Renovators

Location: Chicago, IL

Posted Oct 13, 2025

Well versed in all construction methodologies including the ability to read and interpret contracts, architectural and design drawings, and construction…

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Substation Electrician

Company: Metra

Location: Chicago, IL

Posted Oct 12, 2025

Must have a valid driver's license. Starting pay rates may vary based on entry rates in the Collective Bargaining Agreement (CBA). High School Diploma or GED.

View Details Apply on SimplyHired

Project Manager

Company: HCLTech

Location: Chicago, IL

Posted Oct 11, 2025

Drive solution design and architecture in collaboration with technical stakeholders. Lead the M&A IT integration project, providing strategic guidance to…

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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