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.

CDL-A Truck Driver - 1099 - $5k sign-on bonus

Company: P&S

Location: Chicago, IL

Posted Aug 20, 2025

Truck payment: $500/week to $650/week depending on truck. No credit check, $0 down. Balloon payment at end of term. Earn 70% of line haul.

Cybersecurity Operation Analyst 25-E-03

Company: Illinois Attorney General (IL)

Location: Chicago, IL

Posted Aug 20, 2025

This position requires a bachelor’s degree in Computer Science, Information Systems or Information/Cybersecurity or related field and a minimum 3-5 years’ work…

Business Analyst

Company: Crowe LLP

Location: Chicago, IL

Posted Aug 20, 2025

Ability to effectively communicate technical concepts to non-technical stakeholders. Currently pursuing a bachelor’s or master’s degree in one of the following…

Manager of Sales

Company: ODM Tool & Mfg. Co., Inc.

Location: McCook, IL

Posted Aug 20, 2025

Manage all aspects of the sales and marketing departments, and develop and execute the sales / marketing plans in conjunction with the President and CEO.

Construction Carpenter

Company: PM Construction

Location: Elk Grove Village, IL

Posted Aug 20, 2025

Operate hand tools, power tools, and heavy equipment safely. OSHA 10 or 30 certification preferred. Read and interpret blueprints, sketches, and construction…

Unarmed Security Officer

Company: Per Mar Security Services

Location: Hinsdale, IL

Posted Aug 20, 2025

Must have personal own vehicle! . The selected individual will patrol and secure assigned premises as well as identify risks to staff and patrons.

Incident Analyst

Company: Baer Group

Location: Rosemont, IL

Posted Aug 20, 2025

Ability to work across technical and non-technical teams. Bachelor’s Degree or a related field and 3+ years of IT experience or High school diploma with 6+…

Resource Coordinator Environmental Science Supervisor Manager Level EVS Support Services Environmental Full time Evenings

Company: Northwestern Medicine

Location: Chicago, IL

Posted Aug 20, 2025

Three to five years of experience in relevant field and Supervisory experience. We offer a wide range of benefits that provide employees with tools and…

Maintenance Class A/ Helper A

Company: Community Specialists

Location: Chicago, IL

Posted Aug 20, 2025

Obtain any require city or state certification necessary for maintenance of the property. Safe operation of cleaning equipment, power tools, and hand tools.

Software Development Engineer

Company: Expedia Group

Location: Chicago, IL

Posted Aug 20, 2025

Education: Bachelor’s degree in Computer Science, Software Engineering, or a related field or equivalent related professional experience.

Senior Concrete Finisher / Framer / Layout

Company: Ari Walsh

Location: Berwyn, IL

Posted Aug 20, 2025

Valid DL with a good driving record. Ability to lift up to 50lbs and be comfortable working in outdoor environments/various weather conditions.

Manager Oncology Pharmacy Operations - Outpatient

Company: Rush University Medical Center

Location: Chicago, IL

Posted Aug 20, 2025

Board certification in oncology (BCOP) preferred. 8.Participates in development, implementation, evaluation, and quality improvement of oncology services.

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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