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.

CDL-A Truck Drivers: Regional Home Weekly

Company: U.S. Xpress

Location: Chicago, IL

Posted Jun 24, 2025

CDL A Truck Drivers earn GREAT PAY, consistent miles and 24/7 support with plenty of freight with this truck driving job at U.S. Xpress. $1,000 Sign On Bonus.

Sr. Accountant

Company: Life Tech

Location: Elmhurst, IL

Posted Jun 24, 2025

Prepare and research local and state tax compliance and business registrations. Perform accounting and reporting tasks to support the month end close which…

Project Manager - Owners Rep

Company: Michael Page

Location: Chicago, IL

Posted Jun 24, 2025

Train and develop the project team. Our client is a design/build developer who specialize in K-12 and healthcare projects including but not limited to…

Corporate Accountant

Company: Bel Group

Location: Chicago, IL

Posted Jun 24, 2025

Communicate effectively (both written and verbal) and to develop good working relationships with other employees to accomplish company and departmental goals…

Union Carpenter Apprentice - Chicago, IL

Company: Turner Construction Company

Location: Chicago, IL

Posted Jun 24, 2025

Valid driver’s license preferred. Inspect all tools and power tools before use to ensure they are in safe and working condition.

HVAC/R Service Technician - Light Commercial

Company: CoolSys

Location: Chicago, IL

Posted Jun 24, 2025

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

Developer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Jun 24, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

Sales Consultant

Company: Zeigler Chrysler Jeep Dodge

Location: Downers Grove, IL

Posted Jun 24, 2025

Conduct cold calls to generate leads and build a strong customer base. In this role, you will be instrumental in driving sales and providing exceptional…

Audit QC Director

Company: Porte Brown, LLC

Location: Elk Grove Village, IL

Posted Jun 23, 2025

BA/BS Degree in Accounting, Finance, or related field· CPA Certification · 8+ years of current public accounting experience· 2+ years of current public…

Digital Marketing Technology Specialist – Front-End Web (UX/Design Focus)

Company: Chamberlain Advisors LLC

Location: Chicago, IL

Posted Jun 24, 2025

The ideal candidate will have experience collaborating with creative and technical teams to build seamless, responsive user experiences and maintain a high…

Senior Project Manager- Light Industrial - Downtown Chicago

Company: Michael Page

Location: Chicago, IL

Posted Jun 24, 2025

5+ years as a construction Project Manager for a commercial general contractor. Communicate regularly with owners, construction managers, other superintendents,…

Plumbing Service Technician

Company: Lopez Plumbing Systems

Location: Chicago, IL

Posted Jun 24, 2025

We service mainly commercial/industrial customers throughout the Chicagoland area with some residential customers every so often. Expected hours: 40 per week.

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