Flexible Work Arrangements Jobs in Chicago, IL

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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.

Regional CDL-A Truck Driver, 66+ CPM

Company: Dollar General

Location: Chicago, IL

Posted Jul 23, 2025

1+ years CDL A driving experience. Must be 21 years of age. Experience preferred, requirement based on location. Short term and long term disability.

Client Service Representative

Company: LR WINDSOR Inc

Location: Chicago, IL

Posted Jul 22, 2025

State insurance license (Property & Casualty or Life & Health) must be obtained prior to start date. Previous experience in insurance, customer service, or a…

Plumber

Company: VanDerBosch Plumbing

Location: Chicago, IL

Posted Jul 22, 2025

Must have a valid driver’s license and a clean driving record. Your field experience with current plumbing license and certifications.

Senior Manager, Software Engineer

Company: Capital One

Location: Chicago, IL

Posted Jul 23, 2025

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

Program Manager HCM (Dayforce)

Company: CAI

Location: Chicago, IL

Posted Jul 22, 2025

Monitor project progress, identify potential risks, and implement mitigation strategies to minimize business disruption.

3rd shift Paint Line Machine Operator

Company: PeopleShare

Location: Bensenville, IL

Posted Jul 22, 2025

Operate production machinery and tools to aid the manufacturing process. Perform quality checks using gauges/tools and document production data (e.g., COAs,…

Substation Electrician

Company: Metra

Location: Chicago, IL

Posted Jul 23, 2025

Must have a valid driver's license. Starting pay rates may vary based on entry rates in the Collective Bargaining Agreement (CBA). High School Diploma or GED.

Financial Control Accountant - Chicago, IL

Company: ADM

Location: Chicago, IL

Posted Jul 22, 2025

Financial wellness – flexible spending accounts, health savings account, 401(k) with matching contributions and cash balance plan, discounted employee stock…

Controller - Chicago, IL - Part-Time

Company: Your Part-Time Controller, LLC

Location: Chicago, IL

Posted Jul 23, 2025

4 WEEKS PAID TIME OFF, generally consisting of 100 hours paid vacation to start with eligibility for additional vacation based on tenure and a minimum 40 hours…

Sales Associate

Company: Levy Sector

Location: Chicago, IL

Posted Jul 23, 2025

Associates may also be eligible for paid and/or unpaid time off benefits in accordance with applicable federal, state, and local laws.

Project Manager II - Multifamily Projects

Company: Michael Page

Location: Chicago, IL

Posted Jul 23, 2025

Ability to hire, train, develop and manage a team of Project Managers by providing intentional and proactive leadership. Travel to job site 1-2 days a week.

Local Intermodal - CDL-A Truck Driver - Home Daily (ST121)

Company: TST

Location: Chicago, IL

Posted Jul 23, 2025

Valid Class A CDL license. Local Chicago mileage drivers start at $0.62 per mile, plus $20 load pay per load. *Weekend Differentia*l: $0.12 per mile, applicable…

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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