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.

Senior Accountant

Company: Union Tank Car Company

Location: Chicago, IL

Posted Jul 24, 2025

We offer a comprehensive benefits package that may include medical, dental, vision, 401k matching, and more! Understanding of GAAP and ability to create needed…

CDL A Regional Driver - 100% no-touch freight

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

Registered Nurse 1 | Adult Obs | Nights

Company: Rush University Medical Center

Location: Chicago, IL

Posted Jul 24, 2025

16.Demonstrates accountability for own professional practice, including progress toward achievement of annual goals with guidance.

CDL A OTR Driver - get home weekly!

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

Regional CDL A Truck Driver: home at least weekly

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

Area Marketing Manager, Premium Select Hotels

Company: First Hospitality

Location: Chicago, IL

Posted Jul 23, 2025

Oversee portfolio social media efforts, driving following and engagement, fostering collaboration amongst broader marketing strategies.

Regional CDL A Truck Driver

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

Regional CDL A Driver - up to $105,000

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 24, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

Substation Electrician

Company: Metra

Location: Chicago, IL

Posted Jul 24, 2025

Must have a valid driver’s license. Starting pay rates may vary based on entry rates in the Collective Bargaining Agreement (CBA). High School Diploma or GED.

Senior Tax Analyst Indirect Tax

Company: Amrize Building Materials US

Location: Chicago, IL

Posted Jul 24, 2025

Manage state and local audits, working directly with auditors to provide required and requested data, and manage end to end audit process.

Second Shift Custodian

Company: Bennett Day School Inc

Location: Chicago, IL

Posted Jul 24, 2025

Bennett Day School is a progressive independent day school looking for passionate educators with an innovative spirit and rich background in learning and school…

Retail Cosmetics Sales Associate - CHANEL Beaute, Orland Square - Full Time

Company: Macy’s

Location: Orland Park, IL

Posted Jul 24, 2025

Collaboration: Partnership with the total Beauty team to drive sales and deliver the customer experience. Use product knowledge to give expert guidance to each…

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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