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.

Life-Skills Special Education Teacher

Company: The Menta Education Group

Location: Chicago, IL

Posted Apr 21, 2025

Professional Educator's License (PEL) with LBS1 (Special Education Teacher) certification or PEL with Secondary Education and a desire to obtain your Special…

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relocation assistance sign-on bonus health system

Join our established Endocrinology team in South Chicago

Company: Advocate Health

Location: Chicago, Illinois

Posted Apr 27, 2025

View Details Apply on healthecareers.com

Manual Horizontal Boring Mill Operator

Company: Swingmaster Corporation

Location: Franklin Park, IL

Posted Apr 22, 2025

Read and interpret blueprints, technical drawings, and work instructions to determine machining specifications.

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Senior Specialist - Program & Project Management

Company: LTIMindtree

Location: Chicago, IL

Posted Apr 24, 2025

The candidate must lead and manage end-to-end ISO 20022 implementation project, ensuring timely delivery within scope and budget.

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Marketing Manager

Company: Insurance Navy

Location: Bridgeview, IL

Posted Apr 23, 2025

Proficiency in graphic design software such as Adobe Photoshop, Illustrator, or similar tools. Proven experience in Marketing, Digital Marketing, or a related…

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Logistics Customer Service Representative

Company: MSC Mediterranean Shipping Company S.A.

Location: Chicago, IL

Posted Apr 25, 2025

Prolonged periods sitting at a desk and working on a computer. Additionally, maintaining accurate logs of all transactions in the company's systems is crucial…

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CNC Mill Machinist

Company: ERA Industries LLC

Location: Elk Grove Village, IL

Posted Apr 21, 2025

Ability to use measuring tools including, but not limited to, micrometers, calipers, thread gages, bore gages, dial and test indicators and height gages.

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Solo OTR CDL-A Truck Drivers: $1,000 Sign On Bonus!

Company: U.S. Xpress

Location: Chicago, IL

Posted Apr 25, 2025

Consistent Miles & Freight with this truck driving job. Flex Fleet drivers must live within 250 miles of a U.S. Xpress terminal. Now with $1,000 Sign On Bonus!

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Corporate Tax Accountant

Company: Expansive

Location: Chicago, IL

Posted Apr 24, 2025

Maintain compliance with all multi-state income and franchise tax requirements, including entity-related taxes as well as payroll / employer / employee-related…

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hospital holidays

Breast Sonographer - $40-60 per hour

Company: Advocate Aurora Health

Location: Chicago, Illinois

Posted Apr 21, 2025

View Details Apply on healthecareers.com
hospital staffing agency full time

Travel Emergency Room RN - $1,620 per week

Company: Travel Nurses, Inc.

Location: Chicago, Illinois

Posted Apr 21, 2025

View Details Apply on healthecareers.com

Retail Sales and Store Support

Company: Jewel Osco

Location: Chicago, IL

Posted Apr 28, 2025

Health and welfare benefits for eligible employees (Medical, Dental, 401k and more!).

View Details Apply on SimplyHired

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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