Flexible Work Arrangements Jobs in Chicago, IL

74,517 open positions · Updated daily

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 Truck Driver - weekly minimum pay guarantee

Company: Zeller Transportation

Location: Orland Park, IL

Posted Oct 02, 2025

Right now, we have regional truck driver opportunities open with high earning potential, generous bonus programs, excellent benefits and steady weekly home time…

Graphic Designer

Company: Sherwin-Williams

Location: Chicago, IL

Posted Oct 03, 2025

Graphic design for a wide range of communications, from print to web. Proactively investigate complications and seek solutions to design challenges, while…

DPI Global Cybersecurity IAM Associate Analyst Apprentice

Company: UL Solutions

Location: Chicago, IL

Posted Oct 02, 2025

Participate in IAM-related projects, contributing to tasks such as understanding current state, gathering requirements, documenting future state, coorrdinating…

Manager, Business Continuity

Company: BMO Financial

Location: Chicago, IL

Posted Oct 03, 2025

Typically between 5 - 7 years of relevant experience and post-secondary degree in related field of study or an equivalent combination of education and…

Union Concrete Carpenter

Company: Power Construction

Location: Chicago, IL

Posted Oct 03, 2025

Proficiently use a range of carpenter's hand tools and power tools for cutting, assembling, and finishing tasks.

Cybersecurity & Compliance Analyst

Company: InMarket

Location: Chicago, IL

Posted Oct 02, 2025

Partner with GCP (primary) and AWS engineering teams to design and enforce secure configurations, IAM models, and network controls.

Union Carpenter

Company: Power Construction

Location: Chicago, IL

Posted Oct 03, 2025

Carpenters are responsible for construct, erect, install, and repair structures and fixtures of wood, plywood, and wallboard, using carpenter's hand tools and…

DPI Business Data Analytics Apprentice – IT

Company: UL Solutions

Location: Chicago, IL

Posted Oct 02, 2025

Collaborate with stakeholders to gather and document business and technical requirements. Exposure to data visualization tools (e.g., Power BI, Tableau) or SQL.

Welder

Company: Finzer Roller Inc

Location: Chicago, IL

Posted Oct 03, 2025

You will be expected to read and interpret blueprints and technical drawings to understand project requirements and ensure precision in your work.

Product Content Marketing Specialist

Company: Commusoft

Location: Chicago, IL

Posted Oct 03, 2025

You develop and execute strategies to drive organic traffic growth and improve conversion rates. You use data and reporting tools (e.g., Google Analytics,…

CDL-A Truck Driver - weekly minimum pay guarantee

Company: Zeller Transportation

Location: Chicago, IL

Posted Oct 02, 2025

Right now, we have regional truck driver opportunities open with high earning potential, generous bonus programs, excellent benefits and steady weekly home time…

DPI Global Cybersecurity Compliance Analyst Apprentice

Company: UL Solutions

Location: Chicago, IL

Posted Oct 02, 2025

BS or MA in Business, Computer Science, Information Security, or a related field. Assist with developing and maintain compliance and risk monitoring mechanisms…

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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