Flexible Schedule Jobs in Chicago, IL

34,503 open positions · Updated daily

Looking for Flexible Schedule jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Flexible Schedule position in the Chicago, IL area.

Handyman/plumber

Company: Premier water and sewer

Location: Chicago, IL

Posted Jun 26, 2025

Utilize tools and equipment safely and effectively to complete repairs. Conduct inspections to identify issues requiring attention or repair.

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…

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,…

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.

Registered Nurse

Company: Pearl of Hinsdale

Location: Hinsdale, IL

Posted Jun 25, 2025

Prepare & administer medications as ordered by the physician. Admit, transfer and discharge residents as required. Current Illinois Nursing License (Required).

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.

Utilization Review Nurse

Company: Union Health Service

Location: Chicago, IL

Posted Jun 26, 2025

Active IL RN (Registered Nurse) license / Active LPN (License Practical Nurse). Function in accordance with applicable state, federal laws and regulatory…

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 for Flexible Schedule roles by seniority?
Entry‑level positions pay $60k–$80k annually. Mid‑level engineers and data scientists earn $80k–$120k. Senior roles, including lead architects and senior product managers, range $120k–$180k, while executive‑level talent can command $180k–$250k with bonuses and equity.
What skills and certifications are required for a Flexible Schedule tech career?
Remote collaboration tools (Zoom, Slack) and version control (Git) are essentials. Technical stacks vary: developers need proficiency in JavaScript/TypeScript, Python, or Go; DevOps engineers should master AWS, Terraform, and Kubernetes; data scientists must be fluent in Python, R, SQL, and machine‑learning libraries. Certifications like AWS Certified Solutions Architect, Certified ScrumMaster, or Google Cloud Professional Data Engineer boost credibility.
Is remote work a standard option for Flexible Schedule listings?
Yes—most Flexible Schedule roles are fully remote or offer a hybrid model. Companies provide cloud‑based development environments, VPN access, and asynchronous communication protocols, allowing you to work from any location while staying connected to distributed teams.
What career progression paths exist within Flexible Schedule roles?
Start as a junior engineer or analyst, then advance to senior, team lead, or principal engineer. Product managers move from associate to senior PM, then to director or VP of Product. Technical architects can transition to solutions architect or head of engineering, often with increased ownership of strategy and mentoring.
What industry trends are shaping Flexible Schedule job opportunities?
Hybrid work models are becoming standard, driven by AI‑powered scheduling tools that manage availability across time zones. Remote‑first startups and Fortune 500 firms alike offer flexible hours to attract global talent, boosting demand for digital nomads and professionals seeking work‑life balance.

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