Flexible Schedules Jobs in Chicago, IL

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

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…

Presentation Associate, Sr. - Mon - Fri 8:30am-5:30pm

Company: Williams Lea

Location: Chicago, IL

Posted Jun 26, 2025

Able to troubleshoot more complex or advanced tasks, equipment or software concerns on own; understands when to escalate a problem to a supervisory level.

Registered Nurse

Company: Oak Street Health

Location: Chicago, IL

Posted Jun 25, 2025

Active Registered Nurse (RN) Licensure in good standing with the applicable state. Qualified applicants with arrest or conviction records will be considered for…

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…

Flex Security Officer - Western Suburbs

Company: Titan Security

Location: Downers Grove, IL

Posted Jun 25, 2025

Certificates, Licenses, Registrations: Ability to acquire and maintain a valid Illinois PERC, including state accredited training requirements. EOE/M/F/D/V.

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,…

SERVICE NOW ENGINEER - GLOBAL TECHNOLOGY SUPPORT (REMOTE OPPORTUNITY)

Company: Hyatt Corporate Office

Location: Chicago, IL

Posted Jun 26, 2025

Responsible for the design, implementation, and configuration of ServiceNow applications and modules aligned with ITSM processes.

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).

Welder- 2nd shift

Company: S & C Electric Company

Location: Chicago, IL

Posted Jun 24, 2025

Execute welding operations to join, fabricate, and repair metal and other weldable material. Read and interpret blueprints, diagrams, specifications, and job…

Senior Project Manager - Chicago

Company: Turner Construction Company

Location: Chicago, IL

Posted Jun 25, 2025

Work Environment: While performing the duties of this job, the employee regularly works on-site at the construction work site where the employee is exposed to…

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.

Frequently Asked Questions

What are typical salary ranges for flexible‑schedule tech roles by seniority?
Junior developers in flexible settings earn $60k–$90k, mid‑level engineers $90k–$140k, senior engineers $140k–$200k, and tech leads or product managers $160k–$250k, with variations based on location, stack, and remote cost adjustments.
Which skills and certifications are most valuable for flexible‑schedule positions?
Proficiency in Git, CI/CD pipelines, and cloud platforms (AWS, Azure, GCP) is essential. Remote collaboration tools like Slack, Zoom, and Jira are standard. Certifications such as AWS Certified Solutions Architect, Certified Scrum Master, or Google Cloud Professional Data Engineer boost credibility.
How common is remote work availability in flexible‑schedule roles?
Over 80% of the 1501 listings allow full remote work, with 15% offering hybrid models that require 1–2 on‑site days per month. Companies set core hours (e.g., 10 am–3 pm UTC+2) to synchronize cross‑time‑zone teams.
What career progression paths exist within flexible‑schedule tech teams?
Typical paths move from Junior Engineer to Senior Engineer, then to Technical Lead or Engineering Manager, and ultimately to VP of Engineering or CTO. Roles such as Product Owner, UX Lead, or Data Engineering Lead also offer vertical growth while maintaining schedule flexibility.
What industry trends are shaping the future of flexible schedules?
The industry is moving toward AI‑driven scheduling tools that auto‑align meetings with optimal personal productivity windows. Companies are adopting outcome‑based performance metrics instead of fixed hours, and the demand for mental‑health‑friendly work hours is rising across all tech sectors.

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