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.

CDL-A Regional Truck Driver

Company: G&D Integrated

Location: Chicago, IL

Posted Aug 05, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

Information Security Analyst

Company: K2 Integrity

Location: Chicago, IL

Posted Aug 05, 2025

Any security certification or progress towards a certification is a plus. At least five years’ experience in the information security field.

HR Data Analyst, North America

Company: Aon Corporation

Location: Chicago, IL

Posted Aug 05, 2025

Aon offers a comprehensive package of benefits for full-time and regular part-time colleagues, including, but not limited to: a 401(k) savings plan with…

Project Manager II - Multifamily Projects - Chicago

Company: Michael Page

Location: Chicago, IL

Posted Aug 05, 2025

Ability to hire, train, develop and manage a team of Project Managers by providing intentional and proactive leadership. Travel to job site 1-2 days a week.

CDL-A Truck Driver (Regional OTR): Comprehensive Benefits

Company: G&D Integrated

Location: Chicago, IL

Posted Aug 05, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

Glass Project Manager

Company: MTH Industries

Location: Hillside, IL

Posted Aug 05, 2025

This role requires strong technical knowledge, organizational skills, and the ability to coordinate teams across design, procurement, fabrication, and field…

Janitor Non Union

Company: HABITAT COMPANY LLC

Location: Chicago, IL

Posted Aug 05, 2025

Full time maintenance or janitorial experience, or experience in related field. Conduct all business in accordance with The Habitat Company’s policies and…

Controller

Company: Creative Financial Staffing

Location: Chicago, IL

Posted Aug 05, 2025

Ensure compliance with all regulatory reporting requirements, including 990s, 1099s, state cost reports, and sales tax filings.

Regional CDL-A Driver: Home Weekly

Company: G&D Integrated

Location: Chicago, IL

Posted Aug 05, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

General Accountant

Company: Marriott International, Inc

Location: Chicago, IL

Posted Aug 05, 2025

Speak with others using clear and professional language; prepare and review written documents accurately and completely; answer telephones using appropriate…

State-Certified HVAC Contractor/Installer (Manual J Expert)

Company: Green Attic Insulation

Location: Mount Prospect, IL

Posted Aug 05, 2025

*Valid driver’s license* with a clean driving record. *State-approved HVAC certification/license.*. We are seeking a highly skilled and state-certified HVAC…

Customer Engineer III, Applied AI, Public Sector

Company: Google

Location: Chicago, IL

Posted Aug 05, 2025

Master's degree in Computer Science, Engineering, Mathematics, or a technical field. Identify and qualify business opportunities and key customer technical…

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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