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.

Statistical Analyst, ISS (Entry Level)

Company: American Property Casualty Insurance Association

Location: Chicago, IL

Posted Jul 11, 2025

Under general supervision, the entry-level Statistical Analyst position will review, correct, and approve company data submissions for one or more insurance…

Project Manager

Company: Sidley Austin LLP

Location: Chicago, IL

Posted Jul 11, 2025

Demonstrated knowledge and execution of project management practices, tools and methodologies, including an appropriate project management tool (Smartsheet,…

CDL-A Truck Driver - Regional OTR

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 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…

Senior Manager, Software Engineering, Back End (Go/Python/Java, Node, Jenkins, AWS, DevOps)

Company: Capital One

Location: Chicago, IL

Posted Jul 11, 2025

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

culinary chef manager - Starbucks Reserve Kitchen

Company: Starbucks

Location: Chicago, IL

Posted Jul 11, 2025

Drive the implementation of company programs by developing action plans and directly motivate and instruct kitchen teams to implement and meet operational and…

Data Analyst - Insurance

Company: WAHVE

Location: Chicago, IL

Posted Jul 11, 2025

Compile and prepare data for customer analysis. *Experience* *working in a data analysis role in the insurance or financial services industry – *_*required*_.

Commercial HVAC Preventative Maintenance Technician

Company: BGIS

Location: Chicago, IL

Posted Jul 11, 2025

Subject to drug, background, and driver’s license checks. Maintaining the company service vehicle, tools, and inventory stock while adhering to company driving…

CDL-A Truck Driver - Regional OTR - Up to $105k/yr

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 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…

CDL-A Truck Driver - Regional OTR - Comprehensive Benefits

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 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…

CDL-A Truck Driver - Regional OTR - Home Weekly

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 2025

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

Customer Service Agent - Full Time

Company: MedSpeed

Location: Elmhurst, IL

Posted Jul 11, 2025

Handle a large number of calls daily without losing enthusiastic voice and attitude, answering all calls promptly and efficiently.

Staff Product Security Engineer - AI

Company: Match Group

Location: Chicago, IL

Posted Jul 11, 2025

Experience with various prompt engineering techniques and AI models to effectively develop tooling. Bachelor’s Degree in Computing Science or related field.

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