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.

CNC Machinist

Company: C&A Tool Engineering

Location: Chicago, IL

Posted Jul 24, 2025

Ability to set up CNC: Grinding / Lathe / Mill / Swiss from start to finish including prepping of tools. Hand toolpath programming (angles/radii).

Repairman / Jack Of All Trade

Company: Molly Maid of Oak Park and the Midwestern Suburbs

Location: La Grange, IL

Posted Jul 24, 2025

Doors & Windows – Installation and repair of all door types (interior, exterior, sliding, storm), weather stripping, locks, trim, and basic window repairs or…

Software Engineer

Company: CACI

Location: Lisle, IL

Posted Jul 24, 2025

Participate in technical activities spanning multiple technical disciplines including security analysis, software/tool development, software test, development…

Repairman / Jack Of All Trade

Company: Molly Maid of Oak Park and the Midwestern Suburbs

Location: Hinsdale, IL

Posted Jul 24, 2025

Doors & Windows – Installation and repair of all door types (interior, exterior, sliding, storm), weather stripping, locks, trim, and basic window repairs or…

AI Prompt Engineer

Company: ActiveCampaign

Location: Chicago, IL

Posted Jul 24, 2025

This is a hands-on role focused on prompt design, workflow implementation, and knowledge asset creation, with a goal of delivering repeatable, high-quality…

Manual Lathe Machinist II

Company: American Roller Company

Location: Chicago, IL

Posted Jul 24, 2025

Along the way, you’ll develop technical, mechanical, and problem-solving skills that open doors. Blueprint Reading: Interpret technical drawings and follow…

Chef de Partie

Company: Midosuji at Chicago Athletic Association

Location: Chicago, IL

Posted Jul 24, 2025

During service, this is a guest-facing role where the cook will interact directly with guests and serve dishes across the counter.

Service Plumber

Company: Deljo Heating and Cooling

Location: Chicago, IL

Posted Jul 24, 2025

Valid driver's license with an insurable driving record. 2+ years of plumbing field experience and installation experience. Willing to invest in tools.

Operator - Pail Assembly - 1st Shift

Company: Mauser Packaging Solutions

Location: Chicago, IL

Posted Jul 24, 2025

Inside conditions, extremes of heat (100+ seasonal), exposure to humidity, working in tight areas, high noise levels from production environment, including some…

Laborer Foreman

Company: M. A. Mortenson Company

Location: Chicago, IL

Posted Jul 24, 2025

Ability to work with tools and equipment such as power and non-powered hand tools, vibrators, pumps, drills, and jackhammers; ability to work with machinery…

Digital Graphic Designer

Company: Moody Bible Institute

Location: Chicago, IL

Posted Jul 24, 2025

Bachelor’s or master’s degree in graphic design, digital media production, journalism, or similar communication field.

Machine Operator

Company: Onin Staffing

Location: Hodgkins, IL

Posted Jul 24, 2025

Set up machines for production. Plus, radically affordable health insurance after 30 days. Competitive pay rates 1st shift $18.50per hour.

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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