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.

Security Officer

Company: Vistas of Lincoln Park

Location: Chicago, IL

Posted Jul 30, 2025

Your work will ensure our residents receive the high standard of care they have grown to expect at Vistas of Lincoln Park by monitoring the facility for any…

Owner Operator Truck Driver

Company: HTA Transpotation INC

Location: Chicago, IL

Posted Jul 30, 2025

Proven experience (2 years) in commercial driving with a valid driver's license (CDL required). As an Owner Operator, you will have the flexibility to manage…

Armed Driver Guard

Company: Loomis Armored US, LLC

Location: Chicago, IL

Posted Jul 30, 2025

With a network of nearly 200 branches, Loomis armored transportation, cash management centers, and cash inventory vaults keep cash flowing throughout financial…

Project Manager, Supply Chain Continuity

Company: Ferrara Candy Company, Inc.

Location: Chicago, IL

Posted Jul 30, 2025

Financial analysis and/or cost accounting experience within a manufacturing business. Knowledge of technical functions such as planning, procurement,…

Powder Coat Painter

Company: PROMAN

Location: Chicago, IL

Posted Jul 30, 2025

Proficient in using various power tools related to the painting trade. Operate power tools and machinery safely and effectively during the painting process.

Fine Jewelry Sales and Project Management

Company: Christopher Duquet Fine Jewelry Design

Location: Evanston, IL

Posted Jul 30, 2025

Knowledge of social media platforms and digital marketing strategies. Work in a boutique environment where you can make a real impact on client relationships…

Now Hiring Grill Chefs

Company: Hawksmoor - Chicago

Location: Chicago, IL

Posted Jul 30, 2025

In this role, you’ll be responsible for working with and managing the charcoal grill to prepare high-quality, perfectly grilled meats, seafood, and vegetables…

Security Officers - Full Time - $22.15/hr

Company: Sunstates Security

Location: Northlake, IL

Posted Jul 30, 2025

The Security officer must read and become extremely knowledgeable of Post Orders and SOP and will be able to act quickly and efficiently according to such…

Service Technician Trainee Roofing

Company: Complete Bldg Maint Co

Location: Lombard, IL

Posted Jul 30, 2025

This entry-level position is ideal for individuals looking to develop their skills in the commercial roofing repair, and maintenance field.

Assistant Director, Event and Program Marketing

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 30, 2025

This position demands a blend of creativity, analytical skills, and project management expertise, with strong writing abilities to effectively promote topics…

Assistant Director, Content

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 30, 2025

Minimum requirements include a college or university degree in related field. Bachelor’s degree in a writing-related field such as journalism, English, or…

Artificial Intelligence/Machine Learning (AI/ML) Engineer

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 30, 2025

Minimum requirements include a college or university degree in related field. Acts as a technical consultant and resource for faculty research, teaching, and/or…

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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