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.

Armed Security Guard

Company: GARDAWORLD FEDERAL SERVICES LLC

Location: Norridge, IL

Posted Oct 08, 2025

Must possess a valid driver's license and reliable transportation to the assigned site. Must possess and maintain an active State Security Guard License for the…

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MARKETING MANAGER

Company: Eurest

Location: Elmhurst, IL

Posted Oct 07, 2025

Holiday Time Off (varies by site/state). Associates may also be eligible for paid and/or unpaid time off benefits in accordance with applicable federal, state,…

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2nd Shift CNC Machinist (10% Shift Diff - Direct Hire)

Company: Arsenal Recruiting

Location: Elk Grove Village, IL

Posted Oct 07, 2025

CNC Mill Experience (3-5 Axis). Fanuc, Siemens or Okuma experience preferred. Comfortable editing G & M codes. -10% Shift Differential for 2nd Shift!*.

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Software Engineer

Company: Spraying Systems Co

Location: Glendale Heights, IL

Posted Oct 07, 2025

*Modern Tooling*: Utilize tools like *Git* for version control and AI-powered coding assistants such as *GitHub Copilot* and *Claude Code*.

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Marketing Operations Manager

Company: Ulta Beauty, Inc.

Location: Bolingbrook, IL

Posted Oct 08, 2025

This role, reporting to the Director, Marketing Operations, will be responsible for driving efficiencies across the team, driving forward new process creation,…

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401(k) dental insurance disability insurance

Patient Care Technician - AP4 Med/Surg/Tele - Nights

Company: Endeavor Health

Location: Chicago, Illinois

Posted Oct 07, 2025

View Details Apply on healthecareers.com

Registered Nurse (RN) - Per Diem Days

Company: Rush Specialty Hospital

Location: Chicago, IL

Posted Oct 08, 2025

Initial and ongoing systematic patient assessment. Interpret assessment/diagnostic data including labs and telemetry. Compensation: $56 per hour.

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Flex Security Officer - On-Call - $18.50/hr

Company: Sunstates Security

Location: Burr Ridge, IL

Posted Oct 07, 2025

The flex officer provides trained, competent support by working shifts which become open due to illness, call-offs, weather, vacation, or other causes.

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Staff Pharmacist - Chicago, IL, Amazon Pharmacy

Company: PillPack, LLC

Location: Chicago, IL

Posted Oct 07, 2025

Active and unrestricted Pharmacist License in the state in which you are employed, and others upon request. Answer clinical questions, provide clinical guidance…

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401(k) continuing education credits dental insurance

Respiratory Therapist - Evenings

Company: Endeavor Health

Location: Chicago, Illinois

Posted Oct 07, 2025

View Details Apply on healthecareers.com

BUSINESS DATA ANALYST(EXECUTIVE I)

Company: State of Illinois

Location: Chicago, IL

Posted Oct 07, 2025

The ideal candidate will be comfortable working with large data sets, command-line analysis, and design thinking. 3 paid personal business days per year.

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Customer Service Representative

Company: Roto-Rooter Services Company

Location: Lombard, IL

Posted Oct 08, 2025

Data entry, including customer contact information and relevant details concerning their plumbing problems. Be a trusted informational resource for Roto-Rooter…

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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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