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.

C# Engineer

Company: BlackRock Investments

Location: Chicago, IL

Posted Aug 06, 2025

Participate in cross-functional feature requirements gathering, design, and implementation. You will collaborate with experienced engineers to develop and…

CDL-A Truck Driver - 1099 - Up to $5,000 / week

Company: P&S

Location: Chicago, IL

Posted Aug 06, 2025

Truck payment: $500/week to $650/week depending on truck. No credit check, $0 down. Balloon payment at end of term. Earn 70% of line haul.

Global Practice Architect, Infrastructure III, Google Cloud

Company: Google

Location: Chicago, IL

Posted Aug 06, 2025

You will orchestrate across numerous contributing teams including solutions, services, partners, product engineering, marketing, and GTM stakeholder…

Senior Manager, Software Engineering, Back End (Java, Node, AWS)

Company: Capital One

Location: Chicago, IL

Posted Aug 06, 2025

That includes everything from credit assessment and terms decisioning, to invoicing and payment processing, to servicing, collections and cash application.

CDL-A Truck Driver: Company or 1099

Company: P&S

Location: Chicago, IL

Posted Aug 06, 2025

Truck payment: $500/week to $650/week depending on truck. *Top drivers earn up to $90,000 per year*. No credit check, $0 down. Balloon payment at end of term.

Python Developer

Company: BlackRock Investments

Location: Chicago, IL

Posted Aug 06, 2025

Participate in cross-functional feature requirements gathering, design, and implementation. You will collaborate with experienced engineers to develop and…

Senior Security Governance, Risk & Compliance (GRC) Analyst

Company: Boeing

Location: Chicago, IL

Posted Aug 06, 2025

This role focuses on configuration, administration, and ongoing support to ensure effective cybersecurity risk visibility and reporting striving for highest…

Senior Software Engineer, Full Stack

Company: Capital One

Location: Chicago, IL

Posted Aug 06, 2025

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

Dump Truck Driver

Company: Hana Transport Inc.

Location: Chicago, IL

Posted Aug 06, 2025

Valid commercial driver's license (CDL A) with, 3+ years experience in dump/must have a clean CDL License with no more than 2 tickets in the past 3-years.

Tool Room Machinist 1st shift)

Company: Klein Tools

Location: Elk Grove Village, IL

Posted Aug 06, 2025

Fits and assembles parts into complete assembly, using jigs, fixtures, surface plates, surface table, hand tools and power tools. Ability to weld is a plus.

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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