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.

Affiliate Marketing Director- Legal/Motor Vehicle Accident Leads

Company: The Driscoll Firm, LLC

Location: Chicago, IL

Posted Jul 31, 2025

This is a rare opportunity to *build and own a direct affiliate channel* from the ground up—no middlemen, no third-party networks—just performance, transparency…

Substitute Teacher

Company: Swing Education

Location: Evanston, IL

Posted Jul 31, 2025

No early morning phone calls. $180-$240 per day depending on school, location, and certification. We support substitute teachers with helpful tools, optional…

Substitute Teacher

Company: Swing Education

Location: Chicago, IL

Posted Jul 31, 2025

No early morning phone calls. $180-$240 per day depending on school, location, and certification. We support substitute teachers with helpful tools, optional…

Streets & Utilities - Laborer

Company: Village of Lincolnwood

Location: Lincolnwood, IL

Posted Jul 31, 2025

Work involves performance of a variety of tasks which may include maintenance and repair of Village water and sewer lines.

IT Security & Controls Analyst

Company: Lawson Products

Location: Chicago, IL

Posted Jul 31, 2025

Undergraduate degree in engineering, computer science, or other technical discipline, plus five to seven years of security-specific experience, with at least…

HVAC Commercial Service Technician

Company: Expert Heating Air Conditioning & Plumbing

Location: Downers Grove, IL

Posted Jul 31, 2025

Valid driver's license with a clean driving record for van driving responsibilities. Experience as a field service technician with a focus on customer…

Sous Chef

Company: Gibsons Italia

Location: Chicago, IL

Posted Jul 31, 2025

Train and develop kitchen staff; train cooks/kitchen staff in the importance of consistency in preparation and presentation.

Janitorial Support Team / Floater - Night

Company: Bee Line Support, Inc.

Location: Chicago, IL

Posted Jul 31, 2025

As Bee Line’s front-line cleaning defense, you will perform general cleaning duties, such as cleaning floors, vacuuming rugs, washing walls and glass, and…

Sous Chef

Company: Quartino Ristorante

Location: Chicago, IL

Posted Jul 31, 2025

Train and develop kitchen staff; train cooks/kitchen staff in the importance of consistency in preparation and presentation.

Castline Operator - Machine Operator

Company: Intertape Polymer Group (IPG)

Location: Chicago, IL

Posted Jul 31, 2025

Maintains equipment through the completion of assigned preventative maintenance tasks and minor repair techniques as required. Ability to lift 50 pounds.

HVAC Technician

Company: Temperature Doctors Heating & Cooling, Inc

Location: Chicago, IL

Posted Jul 31, 2025

Valid driver’s license and clean driving record. Must have own hand tools (preferred). Perform diagnostics using schematics and technical documentation.

Custodian

Company: Facilities Performance Group, LLC

Location: Franklin Park, IL

Posted Jul 31, 2025

Adheres to established procedures to provide a safe working environment including complying with OSHA, state/local, federal, and company regulations.

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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