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.

RETAIL SALES ASSOCIATE - YORKTOWN

Company: Ashley

Location: Downers Grove, IL

Posted Jun 18, 2025

Maintain a welcoming, professional, visible presence at the front desk; engage with guests, ensuring they are always treated in a cordial, respectful manner…

Janitor Helper A (SEIU)

Company: Draper and Kramer Inc

Location: Chicago, IL

Posted Jun 17, 2025

Cleaning of common areas may include lobby, fitness center, ballroom, laundry room, restrooms, break room (as applicable).

Maintenance Trades Specialist II, Electrician

Company: Advocate Aurora Health

Location: Oak Lawn, IL

Posted Jun 18, 2025

Trade/Tech School Trades Certificate or trades or industry recognized certification/license requiring Continuing Education Units or periodic renewal to maintain…

Cybersecurity Metrics Analyst

Company: PayPal

Location: Chicago, IL

Posted Jun 18, 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…

Sales Assistant - Large Retail Customers

Company: MACVAD USA

Location: Lincolnwood, IL

Posted Jun 17, 2025

A full driver’s license is required. Data entry, file management and reporting as required. Full-time, permanent role with a global company.

Customer Service, Domestic Services

Company: RIM logistics

Location: Chicago, IL

Posted Jun 17, 2025

RIM logistics, ltd. is a service based company the places the customer experience as the highest priority. Customer Service, Domestic Services representatives…

Residential Plumber Apprentice

Company: LaCassa Plumbing

Location: Westmont, IL

Posted Jun 18, 2025

3+ years of residential plumbing experience. Performance-Based Pay – Earn $22-$50 per hour. Great Benefits – We offer a 401K and health, dental, and vision…

Sous Chef

Company: LUXBAR

Location: Chicago, IL

Posted Jun 18, 2025

Train and develop kitchen staff; train cooks/kitchen staff in the importance of consistency in preparation and presentation.

Cybersecurity Metrics Analyst

Company: paypal

Location: Chicago, IL

Posted Jun 18, 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…

Business Function Implement Practitioner

Company: Experis

Location: Chicago, IL

Posted Jun 17, 2025

Bachelor’s in Supply Chain, Engineering, or related field. Design and support the implementation of o9 solutions. Conduct training and post-go-live support.

VP & Director of Marketing

Company: The Inland Real Estate Group of Companies

Location: Oak Brook, IL

Posted Jun 18, 2025

Bachelor’s degree in Marketing, Business, Real Estate, or a related field; MBA preferred. Partner with the property management leadership team to develop,…

Residential Plumber

Company: LaCassa Plumbing

Location: Westmont, IL

Posted Jun 18, 2025

3+ years of residential plumbing experience. Performance-Based Pay – Earn $80K-$150K/year based on results. Great Benefits – We offer a 401K and health, dental,…

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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