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.

Special Education Teacher (K-12)

Company: Horizon Science Academy Southwest Chicago

Location: Chicago, IL

Posted Aug 28, 2025

Continues to acquire professional knowledge and learn of current developments in the educational field by attending seminars, workshops or professional meetings…

Data Scientist

Company: Havi Supply Chain

Location: Chicago, IL

Posted Aug 28, 2025

Master’s degree in operations research, mathematics, statistics, engineering or closely related field; PhD preferred. Paid parental and medical leave programs.

Substitute Teacher

Company: Swing Education

Location: Chicago, IL

Posted Aug 28, 2025

No early morning phone calls. $160-$180 per day depending on school, location, and certification. We support substitute teachers with helpful tools, optional…

Janitor

Company: Senior Suites of Ravenswood

Location: Chicago, IL

Posted Aug 28, 2025

Assist in cleaning apartments when they transition from a former resident to a new resident. In this role you will maintain the cleanliness of public areas,…

Financial Data Analyst

Company: Respire Home Care

Location: Elmhurst, IL

Posted Aug 28, 2025

Thorough understanding of methods of systems analysis and the principles, design, and procedural methods used in big data analysis.

Union Carpenter

Company: Power Construction

Location: Chicago, IL

Posted Aug 28, 2025

Carpenters are responsible for construct, erect, install, and repair structures and fixtures of wood, plywood, and wallboard, using carpenter's hand tools and…

2nd Grade Teacher - 2025/2026 School Year (Donoghue Campus)

Company: University of Chicago Charter School

Location: Chicago, IL

Posted Aug 28, 2025

Applicant should have a Bachelor’s degree in education and state certification; at least 2 years of urban teaching experience in related field; and proven…

Capital and Project Manager

Company: Liquid Environmental Solutions

Location: Chicago, IL

Posted Aug 28, 2025

Project oriented position with a mix of desk bound (e.g., reviewing capital plans, coordinating project meetings, developing drawings, soliciting bids,…

Janitor Crew

Company: GDI Services Inc US

Location: Skokie, IL

Posted Aug 28, 2025

Must be able to listen to customer requests and follow supervisor instructions. Cleaning of a food manufacturing facility.

Full Time Long Term Care Pharmacist

Company: Care One Pharmacy

Location: Niles, IL

Posted Aug 28, 2025

Conduct patient assessments and collaborate with healthcare teams to develop individualized care plans. Reporting to the General Manager, your role will involve…

PT On-Call Flex Security Officer

Company: St. Moritz Security Services

Location: Chicago, IL

Posted Aug 28, 2025

May require a current state driver’s license, clean driving record as determined by SMSSI, and the ability to safely operate motor vehicle.

Special Education Teacher SY25-26

Company: Noble Schools

Location: Chicago, IL

Posted Aug 28, 2025

Illinois Teaching License (PEL or ELS) with Learning Behavior Specialist I endorsement (LBSI) or out-of-state equivalent of a Special Education teaching license…

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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