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.

Graphic Designer

Company: The School of The Art Institute of Chicago

Location: Chicago, IL

Posted Sep 25, 2025

News and World Report, SAIC provides an interdisciplinary approach to art and design as well as world-class resources, including the Art Institute of Chicago…

Benefits Client Services Representative I

Company: PAYLOCITY CORPORATION

Location: Schaumburg, IL

Posted Sep 25, 2025

The Benefit Account Manager I plays a pivotal role in resolving client payroll and HR system challenges while fostering exceptional customer relationships…

Director of Content Marketing (Remote Available)

Company: S&S Activewear LLC

Location: Bolingbrook, IL

Posted Sep 25, 2025

Define and own go-to-market messaging across all stages of the customer journey, ensuring consistency across web, email, events, sales enablement, catalogs, and…

GenAI Solutions Architect - SFL Scientific

Company: Deloitte

Location: Chicago, IL

Posted Sep 26, 2025

We are hiring a GenAI Solutions Architect to support the technical design, development, and deployment of novel AI solutions across healthcare, life sciences,…

Cyber - Enterprise Security - Microsoft M365 Security Senior Manager

Company: Deloitte

Location: Chicago, IL

Posted Sep 26, 2025

Lead teams documenting platform technical issues, analysis, client communication, and resolution as part of cyber risk mitigation steps.

Industrial Maintenance Electrician | $52+/hr | 1st Shift

Company: Helion Group

Location: Cicero, IL

Posted Sep 25, 2025

*8+ years* of experience in *industrial electrical maintenance*, preferably in a *manufacturing environment*. *Trace and diagnose* control and power circuits to…

Access Control Analyst

Company: HighTower Advisors

Location: Chicago, IL

Posted Sep 25, 2025

Associate’s degree in information technology or Cybersecurity, relevant certifications or related field preferred; or equivalent relevant experience.

Closet Installer

Company: Perfection Custom Closets

Location: Niles, IL

Posted Sep 25, 2025

*Valid driver’s license with clean MVR (Required)*. Read and follow design plans, layouts, and measurements. Ability to safely use hand and power tools.

Commercial/Residential HVAC Service Technician

Company: Air-Rite Heating & Cooling, Inc

Location: Chicago, IL

Posted Sep 25, 2025

This position requires the ability to work independently in the field, manage service calls efficiently, and maintain clear communication with clients and…

Cybersecurity Forensic Analyst - Senior

Company: Huntington Bank

Location: Chicago, IL

Posted Sep 25, 2025

Bachelor's degree in Information Systems, Computer Science or related field preferred. Comply with the organization's cybersecurity policies, procedures among…

Healthcare Data Analyst

Company: The University of Chicago

Location: Chicago, IL

Posted Sep 25, 2025

Master’s degree in biostatistics, computer science, or other related field OR requisite job experience in statistical analysis. Expert in SQL and Excel.

Machine Operator

Company: Elite Staffing

Location: Franklin Park, IL

Posted Sep 25, 2025

May be required to obtain forklift certification. Provide support and guidance to less experienced personnel. Consistently and safely operate extrusion machines…

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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