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.

HVAC Technician (2 local locations)

Company: Lakeshore Sport & Fitness

Location: Chicago, IL

Posted Jul 10, 2025

Willing to use personal basic tools (specialty tools will be provided). Specific knowledge of mechanical, electrical and plumbing systems is also required.

Residential HVAC Installer

Company: Sanchez HVAC Services Inc.

Location: Stickney, IL

Posted Jul 10, 2025

Valid driver’s license and clean driving record. Communicate clearly with customers and answer basic questions about system use and care.

Flat Roofing Foreman in the Chicago Area

Company: EverSeal Roofing

Location: Chicago, IL

Posted Jul 10, 2025

2–3 years’ experience in construction, roofing, or a skilled trade. If you’ve got at least *2 years of team leadership experience* and a background in…

Senior Accountant

Company: Alzheimer's Association

Location: Chicago, IL

Posted Jul 10, 2025

Assist with the entry of annual Budgets. Thorough understanding of developing and working with Excel spreadsheets. Full time or Part time: Full Time.

Maintenance Employee 2nd shift

Company: Fenwick High School

Location: Oak Park, IL

Posted Jul 10, 2025

Kitchen inspections and pest control. Dusting of furniture, equipment, partitions, classroom desks and offices. Cleaning and disinfecting bus fleet.

Manager of Grants Accounting

Company: BEDS Plus, Inc.

Location: La Grange, IL

Posted Jul 10, 2025

Build in system of double checks and internal audits for grant billing and submissions. Update accounting system and all relevant trackers for grant billing and…

RETAIL SALES ASSOCIATE

Company: Ashley

Location: Niles, IL

Posted Jul 10, 2025

Maintain a welcoming, professional, visible presence at the front desk; engage with guests, ensuring they are always treated in a cordial, respectful manner…

Maintenance Electrician - 1st and 2nd Shift

Company: JobSquad Staffing Solutions

Location: Chicago, IL

Posted Jul 10, 2025

Maintain, troubleshoot, and repair electrical and mechanical equipment, including motors, conveyors, PLCs, and control systems. Pay Rate: $40-$44 per hour.

Security Officer (unarmed)

Company: 900 Services, LLC-The Shops at 900

Location: Chicago, IL

Posted Jul 10, 2025

Provide exceptional customer service—greeting guests, assisting with directions, and offering general support as needed.

Regional Manager

Company: Highlands Vista Group

Location: Chicago, IL

Posted Jul 10, 2025

Organize monthly documentation for credit card payments and reimbursement invoices. Assist onsite teams with policy interpretation, compliance, and…

Manufacturing Plant Electricians

Company: JobSquad Staffing Solutions

Location: Chicago, IL

Posted Jul 10, 2025

Maintain, troubleshoot, and repair electrical and mechanical equipment, including motors, conveyors, PLCs, and control systems. 2+ years of PLC experience.

Maintenance Electrician – 1st Shift

Company: JobSquad Staffing Solutions

Location: Chicago, IL

Posted Jul 10, 2025

Maintain, troubleshoot, and repair electrical and mechanical equipment, including motors, conveyors, PLCs, and control systems. 2+ years of PLC experience.

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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