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.

Spray Foam & Drywall/Plaster Installer

Company: Eclipsyum

Location: Schiller Park, IL

Posted Sep 29, 2025

Previous experience in spray foam insulation, drywall installation, plastering, or painting. Install, maintain, and repair drywall and plaster surfaces.

Carpenter / problem solver

Company: Eason Home LLC

Location: Northfield, IL

Posted Sep 29, 2025

Utilize hand tools and power tools for various tasks including trim carpentry, frame carpentry, and fixture installation. Expected hours: 30 – 50 per week.

Client Support Representative

Company: RoofingSource

Location: Niles, IL

Posted Sep 29, 2025

Hungry, resourceful, and looking to develop their skillset within the sales and operations field and learn more about commercial roofing, construction, and HVAC…

Box Truck Driver

Company: Monroe by Maria Lara LLC

Location: Chicago, IL

Posted Sep 29, 2025

Familiarity with route driving and navigating local areas efficiently. Proven experience as a delivery driver or in a similar role is preferred.

Machinist II ( 1,000 Sign On Bonus)

Company: American Roller Company

Location: Riverdale, IL

Posted Sep 29, 2025

*Technical Skills:* Ability to read technical drawings and use micrometers, gauges, and other precision measuring tools. Keep the working area clean and safe.

Leak Detection & Piping Repair Technician - $2,000 Sign On Bonus

Company: Brabazon Pump & Compressor

Location: Chicago, IL

Posted Sep 29, 2025

Must have a valid driver’s license, a clean driving record, a reliable vehicle and proper vehicle insurance. In addition, our tech provides air leak audits at…

Machine Operator I - 2nd Shift

Company: Ferrara Candy Company, Inc.

Location: Forest Park, IL

Posted Sep 30, 2025

Loads trays / boards on truck to be sent to the polishing room. Ability to operate and troubleshoot problems with all necessary process equipment.

Junior Staff Accountant - Full Time

Company: The Nomis Group LLC

Location: Chicago, IL

Posted Sep 29, 2025

Ability to match transactions and identify discrepancies. This role allows the ability for personal & professional growth to help meet your short and long-term…

Data & AI Engineer

Company: Reply

Location: Chicago, IL

Posted Sep 29, 2025

5 years of professional experience in data engineering, AI/ML, or a related technical field. Reply specializes in the design and implementation of solutions…

Data Science Advisors- Hybrid

Company: The Cigna Group

Location: Chicago, IL

Posted Sep 29, 2025

Utilize predictive modeling, segmentation, and machine learning methods to develop technical solutions to increase revenue and margins and provide thought…

Entry Level Business Analyst

Company: Simpalm

Location: Chicago, IL

Posted Sep 29, 2025

Applicants from non-IT and non-computer science background, having good communication and analytical skills can also apply. Excellent verbal and written skills.

Customer Support Representative (Manufacturing)

Company: City Staffing

Location: Chicago, IL

Posted Sep 29, 2025

Field all incoming calls and emails. Bachelor’s degree in a business or technical field. Order entry: 2 years (Required). Customer support: 3 years (Required).

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