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.

Security Agent

Company: SOS Enterprises LLC

Location: Chicago, IL

Posted Aug 11, 2025

All agents must be able to obtain licensing through the Illinois Department of Financial and Professional Regulation, are required to score a minimum of 95%…

Security Officer (Pt)

Company: City Colleges of Chicago

Location: Chicago, IL

Posted Aug 11, 2025

Must have a valid driver’s license, current CPR and/or first aid certification, and hazardous material training. Ability to lift and carry up to 50 pounds.

Construction Management, Project Manager -- Superintendent, Chicago

Company: Bushman Construction Management

Location: Chicago, IL

Posted Aug 10, 2025

0-5+years field experience in commercial construction. Chicago, IL 60630is a general contractor providing complete commercial construction and construction…

CDL-A Truck Driver - Temp-Controlled Freight - up to $1,650/week

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,365/week. *Home weekly* – typically for 48 hours.

Graphic Designer

Company: Kemper

Location: Chicago, IL

Posted Aug 11, 2025

This position will focus on applying best practices in user-centered design and production across various types of print and digital sales collateral.

Lead Finish Carpenter / Architectural Plans Expert

Company: Arkwright Construction

Location: Chicago, IL

Posted Aug 11, 2025

Valid driver's license and dependable transportation. Experience managing subcontractors and directing field crews. Tech Package (Smartphone or Tablet).

School Security Agent

Company: SOS Enterprises LLC

Location: Chicago, IL

Posted Aug 11, 2025

Ensure the safety of staff and student. Ability to operate surveillance equipment. Report on daily activities and any security incidents.

CDL A Dry Van Truck Driver: Home Weekly

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,330/week. *Home weekly* – typically for 48 hours.

Program Manager, Data Centers

Company: JLL

Location: Chicago, IL

Posted Aug 11, 2025

Working collaboratively with various stakeholders, you'll ensure successful program execution while proactively addressing risks and driving operational…

CDL A Truck Driver (Dry Van Freight)

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,330/week. *Home weekly* – typically for 48 hours.

Strategy and Operations Associate, Retail, Product, Go-To-Market

Company: Google

Location: Chicago, IL

Posted Aug 11, 2025

Collaborate cross-functionally across business areas and regions to drive insights and recommendations to leadership and working teams, based on analysis,…

Security Associate

Company: Midwest Goods Inc.

Location: Bensenville, IL

Posted Aug 11, 2025

Have an active CPR and AED Certification valid for at least 2 years. You also manage entry permissions to ensure that only authorized individuals gain access to…

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