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.

Associate Director, Connections Strategy

Company: Rise

Location: Chicago, IL

Posted Jul 15, 2025

You will be a key voice in client relationships, driving clarity around where, how, and why to show up, and ensuring strategies are both inspired and actionable…

Mid-Level Software Developer / Hybrid / Skokie

Company: Motion Recruitment

Location: Chicago, IL

Posted Jul 15, 2025

Bachelor’s degree in computer science (or related field). Sufficient experience as a software engineer (6-8 years). 3+ Years with Angular/TypeScript.

Cash Accountant

Company: Rush University Medical Center

Location: Chicago, IL

Posted Jul 15, 2025

Monitor and reconcile cash transactions, including deposits, bank transfers, and electronic payments daily. Bachelor’s degree in accounting, finance, or related…

Part Time Sales Associate

Company: Paw Naturals

Location: Chicago, IL

Posted Jul 15, 2025

*Provide guests with an exceptional experience.*. Describe any pet experience you have had, whether owning dogs or cats or experience in the pet industry.

Plumber Helper

Company: 24/7 Plumbing & Sewer LLC.

Location: Berwyn, IL

Posted Jul 15, 2025

Utilize hand tools and power tools safely and effectively. Familiarity with hand tools commonly used in construction and plumbing.

Sales Associate

Company: Levy Sector

Location: Chicago, IL

Posted Jul 15, 2025

Associates may also be eligible for paid and/or unpaid time off benefits in accordance with applicable federal, state, and local laws.

Marketplace Digital Marketing Manager

Company: State of Illinois

Location: Chicago, IL

Posted Jul 15, 2025

The Department of Insurance (DOI) regulates the insurance market in the State of Illinois including, but not limited to, licensing and educating insurance…

Registered Nurse (RN) - Hospice

Company: Suncrest Hospice

Location: Oak Park, IL

Posted Jul 15, 2025

Must be willing to drive with reliable transportation, valid driver’s license, and auto insurance, to be able to travel across the service area.

Customer Service Representative, Passenger Service

Company: ALL NIPPON AIRWAYS

Location: Chicago, IL

Posted Jul 15, 2025

Must have a valid Driver's License. Professional presentation and excellent customer service skills. Willing to work any hours/shifts/holidays/weekends and in…

HVAC Refrigeration Service Technician

Company: Nextech

Location: Chicago, IL

Posted Jul 15, 2025

EPA certification and a valid driver’s license. Diagnose and repair HVAC/R systems, including electrical, mechanical, and electronic components.

Driver - Home Daily

Company: Roehl Transport, Inc.

Location: Chicago, IL

Posted Jul 15, 2025

As a dry van truck driver in this driving job, you'll haul freight within a 250-mile radius of our Chicago area terminal.

HVAC/R Service Technician - Light Commercial

Company: CoolSys

Location: Evanston, IL

Posted Jul 15, 2025

Sr, senior, Service Tech, refridgeration, HVAC, refrigeration, HVAC-R, HVAC/R, diagnostic, commercial, service, install, mechanical, mechanic, apprentice, AC,…

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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