Flexible Work Arrangements Jobs in Chicago, IL

74,517 open positions · Updated daily

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.

AI Platform Engineer (GCP) - Remote

Company: The Hartford

Location: Chicago, IL

Posted Jul 07, 2025

Bachelor's degree in Computer Science, Computer Engineering, or a technical field. Manage engineering tasks, driving execution, and optimizing workflows with…

Customer Service Representative

Company: Van DerBosch Plumbing

Location: Chicago, IL

Posted Jul 07, 2025

Help the field team by taking detailed notes from customer calls and entering them into our system. Answer all incoming calls, as the initial point of contact.

Bathroom Remodeling Installer

Company: J. Blanton Plumbing

Location: Northbrook, IL

Posted Jul 07, 2025

Valid plumbing license or current apprenticeship status (apprenticeship sponsorship available). Read and interpret blueprints and technical drawings for…

Data Scientist (Hybrid)

Company: Enova International

Location: Chicago, IL

Posted Jul 07, 2025

At times, you may be asked to conduct ad hoc analysis using statistical and financial tools to recommend for risk management, marketing and operational…

Manager, Media Planning (Traditional and Digital)

Company: Rise

Location: Chicago, IL

Posted Jul 07, 2025

Develop and oversee media strategy, campaign creation, budget, optimization, and testing strategy(ies), as applicable, for full-funnel, multi-platform campaigns…

2nd Shift CNC Machinist

Company: OPW

Location: Skokie, IL

Posted Jul 07, 2025

Benefits: Our total rewards package for eligible team members also includes: a 401(k) savings plan with employer contributions; medical, dental and vision…

Staff Nurse

Company: Union Health Service

Location: Chicago, IL

Posted Jul 07, 2025

Under the direction of the Charge Nurse, the Staff Nurse provides ambulatory care services to patients in all age groups, working with primary care and…

Retail Sales Associate

Company: The Hireverse

Location: Rosemont, IL

Posted Jul 07, 2025

As a *Retail Sales Associate*, you will play a key role in driving sales and providing outstanding customer service.

HVAC Service Technician

Company: Guardian Heating & Cooling Services LLC

Location: Chicago, IL

Posted Jul 07, 2025

Valid driver's license and insurable driving record. Service / maintenance / repair on residential heating and air conditioning systems.

Permanent Substitute Teacher

Company: Oak Park Elementary School District 97

Location: Oak Park, IL

Posted Jul 06, 2025

They establish a positive rapport with students, motivating them to develop the skills, attitudes, and knowledge needed to pursue their full potential.

Controller/Accountant Automotive Dealership

Company: Confidential Car Dealership

Location: Chicago, IL

Posted Jul 07, 2025

Bachelor's degree in Accounting, Finance, or related field; CPA or CMA preferred. Manage the financial planning and analysis process, including forecasting,…

Controller

Company: Housing Opportunity Development Corporation

Location: Skokie, IL

Posted Jul 07, 2025

Daily: Oversee invoice processing, check deposits, data entry, account reconciliation, and records filing. Education: Bachelor’s degree in finance, accounting,…

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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