Flexible Work Schedules Jobs in Chicago, IL

74,598 open positions · Updated daily

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

contract travel 401(k)

Travel Nurse RN - PCU - Progressive Care Unit - $2,218 per week

Company: GHR Healthcare

Location: East Chicago, Indiana

Posted Apr 20, 2025

View Details Apply on healthecareers.com
dental insurance health insurance life insurance

Director of Nursing Operations - Endoscopy

Company: Cook County Health

Location: Chicago, Illinois

Posted Apr 20, 2025

View Details Apply on healthecareers.com

Sales and Marketing Representative

Company: SERVPRO

Location: Broadview, IL

Posted Apr 18, 2025

In this role you will be meeting with potential customers to help develop our customer base and exceed sales goals via route selling, continuing education…

View Details Apply on SimplyHired

Data Analyst - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

You can work on your own schedule. You will measure the progress of these AI chatbots, evaluate their logic, and solve problems to improve the quality of each…

View Details Apply on SimplyHired

Database Developer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

A bachelor’s degree (completed or in progress). Proficiency in at least one of the following programming languages or frameworks: JavaScript, TypeScript, Python…

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Web Engineer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

View Details Apply on SimplyHired

Tax Senior - Financial Services Organization - State and Local Tax - Real Estate

Company: EY

Location: Chicago, IL

Posted Apr 20, 2025

A CPA certification, or good standing as a member of a state bar. Staying abreast of state & local tax developments and work to develop new and innovative…

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Full Stack Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

View Details Apply on SimplyHired
part time full time contract

Travel Interventional Radiology Technologist - $2,281 per week

Company: Supplemental Health Care

Location: Chicago, Illinois

Posted Apr 21, 2025

View Details Apply on healthecareers.com

Tax Services Manager - FSO - GCR/Insurance EDGE

Company: EY

Location: Chicago, IL

Posted Apr 18, 2025

Direct experience in state and local taxation (e.g., state return compliance, state income tax accounting, state apportionment fundamentals).

View Details Apply on SimplyHired

Power BI Developer

Company: Velvetech

Location: Chicago, IL

Posted Apr 18, 2025

Design, develop and support data analytics using Power BI service, self-service models, and visualization tools. Experience with differen large language models.

View Details Apply on SimplyHired

Senior Data Engineer / Analytic Engineer

Company: Velvetech

Location: Chicago, IL

Posted Apr 18, 2025

As a Senior Data Engineer / Analytic Engineer (Microsoft Fabric), you will lead the design, implementation, and optimization of data engineering pipelines and…

View Details Apply on SimplyHired

Frequently Asked Questions

What are the typical salary ranges for Flexible Work Schedules roles at different seniority levels?
Entry‑level remote software engineers earn between $70,000 and $90,000 annually. Mid‑level roles (2‑5 years) range from $90,000 to $120,000. Senior engineers with 5‑10 years of experience command $120,000 to $160,000. Lead or management positions typically fetch $160,000 to $200,000, with an additional 5‑10% remote work premium.
Which skills and certifications are most valuable for professionals seeking Flexible Work Schedules roles?
Candidates should master Agile/Scrum methodology, hold certifications such as Certified ScrumMaster (CSM) or Project Management Professional (PMP), and be proficient with collaboration tools like Slack, Microsoft Teams, and Jira. Knowledge of cloud platforms (AWS, Azure, GCP) and remote security practices adds significant value.
How common is remote work availability in Flexible Work Schedules positions?
Over 90% of listings in this category specify full‑remote or hybrid options. Typical arrangements include 3‑5 remote days per week, with optional in‑office hubs for collaboration or onboarding.
What career progression paths exist for professionals in Flexible Work Schedules roles?
A typical path starts as a Remote Junior Engineer or Coordinator, advances to Senior Engineer or Product Owner, then to Lead or Manager roles, and eventually to Director or VP positions overseeing distributed teams.
What industry trends are shaping Flexible Work Schedules?
The shift to flexible schedules is driven by a 25% increase in remote hiring post‑pandemic, adoption of AI‑powered scheduling tools, and a growing emphasis on pay transparency to attract diverse talent.

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