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.

Senior Lead Software Engineer, Full Stack

Company: Capital One

Location: Chicago, IL

Posted May 01, 2025

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

Data Scientist 1

Company: PayPal

Location: Chicago, IL

Posted May 01, 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…

Senior HVAC Residential Service Technician

Company: Deljo Heating & Cooling

Location: Chicago, IL

Posted May 02, 2025

Valid driver's license and insurable driving record. Consult with customer on repair and replacements. Pay: $40.00 - $50.00 per hour depending on experience +…

Security and Safety Officer - Part Time

Company: Loyola University Health System

Location: Melrose Park, IL

Posted May 02, 2025

General - Valid Illinois driver's license. Specify Degree(s): Criminal Justice, Law Enforcement, Security Admin, Fire Services or related field.

CDL-A Truck Driver - Flatbed Division

Company: Koch Trucking

Location: Oak Park, IL

Posted May 02, 2025

All candidates must have a valid CDL-A license and 12 months of driving experience . Koch Trucking is looking to hire CDL-A truck drivers to join our flatbed…

CDL-A Solo & Team Owner Operator Truck Drivers

Company: Roadrunner

Location: Chicago, IL

Posted May 02, 2025

Connect with Roadrunner to experience the way truck driving business ownership should be. Average weekly pay averages between $2,500-$4,000 for solo drivers, $…

Retail Sales Associate

Company: Korn Ferry RPO for Tempur Sealy

Location: Oak Brook, IL

Posted May 03, 2025

During the first year of employment, your paid time off will be pro-rated based on date of hire unless otherwise dictated by state or local law.

Owner/Operator needed for Dedicated Line-Haul, Melrose Park, IL to Montpelier, OH

Company: BRYAN TRUCK LINE

Location: Melrose Park, IL

Posted May 02, 2025

Proven experience in truck driving with a strong understanding of commercial driving regulations. Ensure compliance with all federal, state, and local…

Licensed Plumber

Company: Deljo Heating & Cooling

Location: Chicago, IL

Posted May 02, 2025

Valid driver's license with an insurable driving record. 5+ years of plumbing field experience and installation experience. Install and upkeep sump pumps.

Senior Software Engineer, Full Stack

Company: Capital One

Location: Chicago, IL

Posted May 01, 2025

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

CDL-A Truck Driver - Flatbed Division

Company: Koch Trucking

Location: Cicero, IL

Posted May 02, 2025

All candidates must have a valid CDL-A license and 12 months of driving experience . Koch Trucking is looking to hire CDL-A truck drivers to join our flatbed…

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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