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.

Carpenter

Company: RedBox Workshop

Location: Chicago, IL

Posted Aug 13, 2025

RedBox Workshop, Chicago’s premier fabricator of children’s interactive museum exhibits, is seeking skilled carpenters with a minimum of two years experience in…

CDL A Company Truck Driver

Company: Dollar General

Location: Chicago, IL

Posted Aug 13, 2025

1+ years CDL A driving experience. Must be 21 years of age. Experience preferred, requirement based on location. Short term and long term disability.

Anthropologie Sales Associate

Company: Anthropologie

Location: Chicago, IL

Posted Aug 13, 2025

A Sales Associate contributes to driving sales through providing a genuine and unique experience to each customer.

ETL Analyst/Data Scientist

Company: UChicago Medicine

Location: Chicago, IL

Posted Aug 13, 2025

Working with both internal and external stakeholders, the ETL Analyst/Data Scientist will design and deliver data models, data structures, and informatics…

CDL A Regional Truck Driver

Company: Zeller Transportation

Location: Chicago, IL

Posted Aug 13, 2025

Right now, we have regional truck driver opportunities open with high earning potential, generous bonus programs, excellent benefits and steady weekly home time…

Public Safety Officer I - Armed (Full Time, 3rd Shift)

Company: Advocate Aurora Health

Location: Chicago, IL

Posted Aug 13, 2025

A valid driver’s license issued by the Division of Motor Vehicle. Responds to service calls, such as combative or threatening patients or visitors and team…

Information Security Risk Analyst - Intermediate

Company: UChicago Medicine

Location: Chicago, IL

Posted Aug 13, 2025

Enhance the organization’s cybersecurity awareness and training efforts by communicating risk insights to technical and non-technical audiences.

Task Force Executive Chef

Company: Hyatt Lodge Oak Brook

Location: Oak Brook, IL

Posted Aug 13, 2025

College degree or certification in culinary field/hospitality field preferred. 4+ years kitchen management experience.

RN Triage - Primary Care - Days

Company: Endeavor Health

Location: Chicago, IL

Posted Aug 13, 2025

Evaluates patient’s and caregiver’s understanding of instructions using teach-back methodology and conveys related information and issues to appropriate…

Plumbers & Drain Techs Wanted (Get your license!)

Company: The Scottish Plumber

Location: Villa Park, IL

Posted Aug 13, 2025

Have a valid driver's license and a clean driving record. Have at least 2 years of plumbing or drain cleaning experience.

Payment Card Industry Data Security Standards (PCI DSS) Risk Analyst

Company: UChicago Medicine

Location: Chicago, IL

Posted Aug 13, 2025

Bachelor's degree required in Information Security, Computer Science, Information Technology, or a related field or equivalent work experience.

CDL A Regional Truck Driver - 66+ CPM

Company: Dollar General

Location: Chicago, IL

Posted Aug 13, 2025

1+ years CDL A driving experience. Must be 21 years of age. Experience preferred, requirement based on location. Short term and long term disability.

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.

Related Pages