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.

Theatrical Head Carpenter

Company: Hubbard Street Dance Chicago

Location: Chicago, IL

Posted Jun 18, 2025

Help supervise crews at both union and non-union venues, leading and participating in truck calls, load-ins, work calls, maintenance calls, technical rehearsals…

Cybersecurity Risk Analyst

Company: PayPal

Location: Chicago, IL

Posted Jun 19, 2025

Translate technical risks into business terms to promote effective communication and develop and coach teams to be able to identify, manage, and escalate risk.

Project Manager

Company: Cherry Talent Group

Location: Chicago, IL

Posted Jun 19, 2025

Comfortable managing both client-facing relationships and internal communication with field staff. Handle bid analysis, RFIs, submittals, change orders, shop…

Finisher Painter

Company: Creative Contractors

Location: Chicago, IL

Posted Jun 18, 2025

Reliable vehicle & valid driver’s license. This role involves working on construction sites, performing both interior and exterior painting tasks.

Commercial HVAC Technician

Company: Longterm Health Management Services

Location: Skokie, IL

Posted Jun 19, 2025

This role requires a strong mechanical aptitude and the ability to work with various HVAC equipment and tools.

Cabinet Maker

Company: New Style Cabinets, Inc.

Location: Chicago, IL

Posted Jun 18, 2025

Ability to use appropriate cutting tools. Reading shop drawings and blueprints. A minimum of 5+ years of experience in high end custom cabinetry IS A MUST (…

Registered Nurse, Ambulatory Peds

Company: Ann & Robert H. Lurie Children’s Hospital of Chicago

Location: Chicago, IL

Posted Jun 19, 2025

Performs nursing assessments utilizing a variety of assessment methods and/or area-specific tools. Basic Life Support certification from the American Heart…

Assistant Carpenter

Company: Chicago Theatre Group Inc

Location: Chicago, IL

Posted Jun 18, 2025

Valid driver’s license required. Work all load out, load in and tech note calls as scheduled by the TD staff. Collaborate with TD staff and other shop staff to…

High-End Jewelry/Timepiece Sales Specialist

Company: Burdeen's Jewelry

Location: Chicago, IL

Posted Jun 18, 2025

Consistently develop client relationships and exceed monthly targets through a passion for building your own successful business.

Ob-Gyn Telephone Triage Nurse--RN

Company: Chicago Women's Health Group

Location: Chicago, IL

Posted Jun 19, 2025

This position will be entirely on the phones triaging incoming calls from patients regarding problems, lab results, prescription refills, orders and additional…

Handyman - Odd Jobs - Carpenter - Painter

Company: Top Notch Handyman LLC

Location: La Grange, IL

Posted Jun 19, 2025

Experience with painting, drywall patching or carpentry is a plus, but we can provide on the job training to those with a willing to learn attitude.

HIS Enterprise Architect

Company: RL Canning

Location: Chicago, IL

Posted Jun 19, 2025

They ensure solutions transition from the current state to target state solutions that achieve business outcomes.

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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