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.

Content Marketing Manager

Company: Epsilon

Location: Chicago, IL

Posted Jul 22, 2025

As a Content Marketing Manager at Epsilon, you will play a pivotal role in driving our marketing efforts through content strategy, SEO, website strategy,…

Senior Manager, Software Engineering, Back End

Company: Capital One

Location: Chicago, IL

Posted Jul 22, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

Trim & Millwork Lead Carpenter

Company: The Contractor Consultants

Location: Chicago, IL

Posted Jul 22, 2025

Valid driver's license and dependable transportation. Experience managing subcontractors and directing field crews. Company Name: Arkwright Construction LLC.

Restaurant Call Center Agent

Company: Paisans Pizzeria

Location: Berwyn, IL

Posted Jul 22, 2025

The successful candidate will be responsible for answering incoming calls from customers, taking orders, and providing excellent customer service.

Sr Accountant

Company: PayPal

Location: Chicago, IL

Posted Jul 22, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

AWS Senior Lead Product Manager (RapidScale)

Company: Cox Communications

Location: Chicago, IL

Posted Jul 22, 2025

The right candidate could also have a different combination, such as a master's degree and 6years' experience; a Ph.D. and 3 years' experience in a related…

Construction Accountant

Company: Devon Self Storage Holdings (US), LLC

Location: Oak Brook, IL

Posted Jul 22, 2025

The Construction Accountant will manage the accounting aspects of construction projects, focusing on recording draw requests, reviewing and classifying vendor…

Interim Controller 16708192

Company: Cordia Resources by Cherry Bekaert

Location: Chicago, IL

Posted Jul 21, 2025

Demonstrated success in managing and developing finance teams. Excellent analytical and strategic thinking skills including strategic consideration and thinking…

Graphic Designer/Marketing

Company: American Classic Tours

Location: Des Plaines, IL

Posted Jul 22, 2025

Social Media Marketing: schedule and post engaging content across our social media platforms. Email Marketing: design weekly eblasts sent to our travelers…

CDL- A Intermodal Truck Driver - Owner Operator - Home Daily

Company: Forward Intermodal

Location: Chicago, IL

Posted Jul 22, 2025

12 months of verifiable tractor trailer experience. Drop & hook and live loads. Forward is partnering with Class A CDL Owner Operators in the Chicago, IL area…

Machine Learning Engineer

Company: BMO US

Location: Chicago, IL

Posted Jul 22, 2025

Works with other data and analytics professionals to optimize, refine, automate and scale analysis into repeatable analytics solutions and decision support…

Senior Software Engineer, Full Stack

Company: Capital One

Location: Chicago, IL

Posted Jul 22, 2025

Collaborate with and across Agile teams to design, develop, test, implement, and support technical solutions in full-stack development tools and technologies.

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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