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.

Marketing Coordinator

Company: ARCO a Family of Construction Companies

Location: Chicago, IL

Posted Jun 26, 2025

We hire the best and the brightest from across the country – constructing a team of experts in architecture, design, engineering, project management, and…

Manager, Marketing FP&A

Company: PayPal

Location: Chicago, IL

Posted Jun 26, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

Graphic Designer (Multimedia Focus)

Company: Daniels Health

Location: Chicago, IL

Posted Jun 25, 2025

Experience with project management and managing project timelines (not only your own, but also of any contractors).

Sr. Software Engineer

Company: Caterpillar

Location: Chicago, IL

Posted Jun 25, 2025

REQS: This position requires a bachelor’s degree, or foreign equivalent, in Computer Science, Computer Engineering, Performance, Information Management, or a…

Personal Chef (Freelance)

Company: CookinGenie LLC

Location: Chicago, IL

Posted Jun 26, 2025

Flexible Scheduling* – You set your own availability and get bookings that work for you. Showcase Your Talent* – Build your profile to highlight your menus,…

Project Manager, Office of Equity

Company: Chicago Public Schools

Location: Chicago, IL

Posted Jun 26, 2025

Build and maintain strong partnerships with school leaders, educators, parents, community organizations, city/state agencies, and other stakeholders to create a…

Social Media Manager - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Jun 25, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). Write high-quality answers when given specific prompts.

Project Manager - Multifamily - Downtown Chicago

Company: Michael Page

Location: Chicago, IL

Posted Jun 26, 2025

Bachelors degree in Construction Management or a related field is preferred. Train and develop the Project team and schedule project resources.

Retail Leasing Associate

Company: Bridge33 Capital

Location: Chicago, IL

Posted Jun 26, 2025

A minimum of 1-2 years’ leasing experience in a retail leasing or marketing role in commercial real estate; property management or related field.

Graphic Designer (Preferably Hindi/Urdu Speaking)

Company: Intense oud

Location: Chicago, IL

Posted Jun 26, 2025

Be able to make videos for social media. Able to learn how to post and use different softwares. Job Types: Full-time, Part-time.

Registered Nurse 2, Antepartum/Postpartum

Company: Rush University Medical Center

Location: Chicago, IL

Posted Jun 26, 2025

17.Demonstrates accountability for own professional practice, including progress toward achievement of annual goals. 2.Maintain current BLS certification.

HVAC Lead Installer

Company: ARS-Rescue Rooter

Location: Chicago, IL

Posted Jun 26, 2025

Valid driver’s license with good driving record. EPA certification (or willingness to obtain). Disassemble and remove outdated HVAC systems, then install, start…

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