Flexible Work Arrangements Jobs in Chicago, IL

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Looking for Flexible Work Arrangements jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Work Arrangements position in the Chicago, IL area.

Security Operations Analyst I

Company: NinjaTrader

Location: Chicago, IL

Posted Aug 21, 2025

Basic knowledge of security tools – firewalls, intrusion detection/prevention systems, SIEM, endpoint detection and response, and common vulnerability…

Switcher/Loader/ Local Driver CDL A

Company: Millenia Aero

Location: Chicago, IL

Posted Aug 21, 2025

Clean driving record - no driving violations in the last 3 years. Minimum 2 years CDL Class A experience. No positive/rejected drug test.

Gold Coast High-Rise Condo Door Staff Second Shift Door Staff

Company: Sudler Property Management

Location: Chicago, IL

Posted Aug 21, 2025

Our Door Staff are the face of our building and the first to greet, welcome, and assist residents, guests, and vendors. Keep the flow of the driveway moving.

Helper A Janitor

Company: Waterton

Location: Chicago, IL

Posted Aug 21, 2025

This includes but is not limited to move-out/move-in inspections, electrical, HVAC, plumbing, carpentry, appliance repairs, carpet cleaning, painting, and…

Senior Business Analyst

Company: Chamberlain Advisors LLC

Location: Chicago, IL

Posted Aug 21, 2025

Bachelor’s degree in computer science, engineering, business, or related field required; MBA or advanced degree preferred.

Customer Activation Specialist

Company: Emery Jensen Distribution, LLC

Location: Oak Brook, IL

Posted Aug 21, 2025

Proactively monitor new and existing customer master data to ensure accuracy; develop ongoing auditing processes to validate customer master data and provide…

DME Customer Service Representative - 2nd Shift

Company: Integra Healthcare Equipment

Location: Elmhurst, IL

Posted Aug 21, 2025

Interacts with customers via telephone and email to provide support and information on rental/sales transactions, and logistics process.

Morning Office Cleaner - Part-Time, Bedford Park, Tuesday & Friday, 12hrs/week

Company: Evergreen Cleaning Group

Location: Bedford Park, IL

Posted Aug 21, 2025

Low-stress, independent work environment. Ability to lift up to 25 lbs and use standard cleaning tools. It’s a great fit for someone looking to earn steady side…

HVAC/Refrigeration Technician

Company: Crothall Healthcare

Location: Chicago, IL

Posted Aug 21, 2025

EPA Refrigeration license and Driver's license (Required). Must have valid driver’s license. Must have valid EPA refrigeration license.

Helper C Janitor

Company: Waterton

Location: Chicago, IL

Posted Aug 21, 2025

This includes but is not limited to move-out/move-in inspections, electrical, HVAC, plumbing, carpentry, appliance repairs, carpet cleaning, painting, and…

Senior Interior Designer/Project Manager

Company: 123 Remodeling

Location: Chicago, IL

Posted Aug 21, 2025

Meet with the client, develop a concept, then work with our design assistants who will render 3-D drawings for you. This is not an entry level position.

Senior Software Engineer (Go/Java/Python, AWS)

Company: Capital One

Location: Chicago, IL

Posted Aug 21, 2025

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

Frequently Asked Questions

What are typical salary ranges by seniority for flexible work arrangement roles?
Junior remote developers earn $70k–$95k, mid‑level professionals earn $95k–$140k, and senior specialists or leads earn $140k–$200k. Remote‑specific allowances can add 5–10% on top of base pay for high‑cost‑of‑living locations.
What skills and certifications are required for flexible work roles?
Core technical skills include Git, Docker, Kubernetes, and proficiency in at least one cloud platform (AWS, Azure, GCP). Remote collaboration skills involve Slack, Zoom, Notion, and Asana. Certifications such as Certified Remote Work Manager, AWS Certified Solutions Architect, Azure Fundamentals, Google Cloud Professional, PMP, or CSM are highly valued.
How widely available are remote work opportunities in this category?
All 2964 positions support remote work, offering full‑time, part‑time, and contract options. Companies provide VPN, zero‑trust security, and remote onboarding tools, enabling employees to start from any location with a reliable internet connection.
What career progression paths exist for professionals in flexible work arrangements?
Typical paths move from Junior Remote Engineer → Senior Remote Engineer → Remote Technical Lead → Remote Engineering Manager or Remote Product Lead. Parallel tracks include Remote UX Lead, Remote Data Lead, or Remote Customer Success Manager, with opportunities to transition into remote operations or CTO roles.
What industry trends are shaping flexible work arrangements?
The remote‑first trend is accelerating, with 60% of tech firms adopting hybrid models by 2025. Adoption of AI‑driven collaboration tools, real‑time code review, and remote cybersecurity protocols is increasing. Companies increasingly offer remote benefits such as home‑office stipends and global health plans, driving higher demand for qualified remote professionals.

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