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.

AI Data Engineer

Company: Crowe LLP

Location: Chicago, IL

Posted Aug 12, 2025

Design, develop, and maintain robust data pipelines and ETL processes that enable the seamless integration, cleansing, harmonization, and transformation of data…

Part-Time Custodian

Company: Nicholas Sportsplex

Location: Mount Prospect, IL

Posted Aug 11, 2025

Assists renters and occupants in a courteous and polite manner. Prepares and clears event spaces, including equipment installation and removal.

PHARMACIST – INPATIENT - CERMAK HEALTH SERVICES

Company: Cook County Health & Hospitals System

Location: Chicago, IL

Posted Aug 11, 2025

Identify self as a Veteran on the employment application by answering yes to the question by answering yes to the question, “Are you a Military Veteran?”.

Bilingual Medical Call Center Representative

Company: Chicago Eye Consultants

Location: Stickney, IL

Posted Aug 12, 2025

Answer telephone calls promptly and in a polite and professional manner. You will be responsible for handling a wide range of inbound and outbound calls,…

Prep Chef | Ghost Donkey | River North

Company: Flagship Restaurant Group

Location: Chicago, IL

Posted Aug 12, 2025

Maintain a clean and organized prep area, ensuring all tools and equipment are sanitized and in good working order.

( E LPT ) Regular Teacher

Company: Chicago Public Schools

Location: Chicago, IL

Posted Aug 12, 2025

ESSENTIAL FUNCTIONS: Responsible for instructional planning, including, but not limited to, providing written lesson plans and preparation in accordance with…

Janitor

Company: LACOSTA Facility Support Services

Location: Melrose Park, IL

Posted Aug 12, 2025

Job duties: Responsible for cleaning the offices, break rooms, stairwells, supply closet, lobby. Wear LACOSTA Shirt, safety glasses, steel-toed boots/shoes,…

AI Security Engineer

Company: Crowe LLP

Location: Chicago, IL

Posted Aug 12, 2025

Excellent communication skills, with the ability to clearly articulate complex security topics to both technical and non-technical audiences.

Security Officer

Company: The Westin Chicago Lombard

Location: Lombard, IL

Posted Aug 12, 2025

Answer security telephone and safety hotline calls and respond in a timely manner based on priority. Handle undesired conduct and potential violations of hotel…

Cleaner/Janitor

Company: Spot-On Cleaning & Removal Service LLC

Location: Rosemont, IL

Posted Aug 11, 2025

\*Special jobs also can be available like High dusting and floor scrubbing if more hours are requested, work is year round weekly ideal for students or someone…

Cap Security- Spencer Technology Academy

Company: Youth Guidance

Location: Chicago, IL

Posted Aug 12, 2025

Field telephone calls as needed. Log visitors and permit entry. We strive to celebrate the unique qualities of youth and recognize them as empowered leaders,…

Janitor 1st Shift

Company: LACOSTA Facility Support Services

Location: Melrose Park, IL

Posted Aug 12, 2025

LACOSTA Facility Support Services, a minority owned business contractor, has been delivering quality facility services for more than 32 years, helping customers…

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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