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.

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Company: DoorDash

Location: Chicago, IL

Posted Sep 17, 2025

Deliver with DoorDash and earn extra cash while being your own boss. Whether you’re looking for a side hustle or a full-time gig, delivering with DoorDash gives…

Associate Brand Manager, Marketing Innovation

Company: Kraft Heinz Company

Location: Chicago, IL

Posted Sep 17, 2025

Bachelor’s Degree (or advanced degree) in Business, Marketing, or related field. Partner with the Marketing & Sales teams to develop compelling product launch…

Solutions Architect

Company: Rotary International

Location: Evanston, IL

Posted Sep 17, 2025

Work on product technical design and feasibility assessments accounting for technical constraints. Design, develop and implement components and templates in…

Entry-Level Sales Associate (Private & Cargo Aviation)

Company: City Staffing

Location: Chicago, IL

Posted Sep 17, 2025

Months 6–12: Pass internal certification and begin independent sales. Support your mentor’s sales desk while training. B2B sales: 3 years (Preferred).

Machine Operator Level 1-2nd Shift

Company: Gold Eagle Co

Location: Chicago, IL

Posted Sep 17, 2025

Relevant experience as a machine operator with basic mechanical skills and aptitude. You’ll also support non-technical tasks such as stacking and packing to…

Systems Engineer - Windows

Company: ComPsych Corporation

Location: Chicago, IL

Posted Sep 17, 2025

Strong communication skills to interact with technical and non-technical stakeholders. The ideal candidate will play a critical role in managing, supporting,…

VP Technology Transformation, Project Management Office

Company: J.S. Held LLC

Location: Chicago, IL

Posted Sep 17, 2025

Champion strategic initiatives, including driving enterprise-wide technology solutions, process optimization, and efficiency gains.

Graphic Designer

Company: International Fellowship of Christians & Jews, Inc

Location: Chicago, IL

Posted Sep 16, 2025

Stay up to date on digital media standards, software, international design considerations, and design trends. Ability to design for different audiences as well…

RN - Home Health-Ukrainian Village

Company: Aspire Home Health Care

Location: Chicago, IL

Posted Sep 17, 2025

Registered Nurse licensed in the state of Illinois. Locations/ Zip Codes you serve are negotiable. Demonstrate working knowledge in Medicare and Medicaid…

Business Intelligence Analyst

Company: Combined Insurance

Location: Chicago, IL

Posted Sep 16, 2025

He/she will work closely with the reporting manager to deliver on the design/development, programming, maintenance, and publication of operational reports that…

Market Director of Clinical Services

Company: LiveWell Choice, LLC

Location: Chicago, IL

Posted Sep 17, 2025

Valid state driver's license with a good driving record and proof of automobile insurance required. State unrestricted licensed Advanced Practice Nurse and…

Deputy Controller

Company: Paradigm Healthcare

Location: Skokie, IL

Posted Sep 17, 2025

Strong work ethic and commitment to the profession demonstrated by possessing a Certified Public Accountant license and maintaining their certification with…

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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