Flexible Schedules Jobs in Chicago, IL

27,628 open positions · Updated daily

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.

CDL-A Truck Drivers: Regional Home Weekly

Company: U.S. Xpress

Location: Chicago, IL

Posted Jun 24, 2025

CDL A Truck Drivers earn GREAT PAY, consistent miles and 24/7 support with plenty of freight with this truck driving job at U.S. Xpress. $1,000 Sign On Bonus.

Chef de Cuisine - Restaurants

Company: Eataly North America

Location: Chicago, IL

Posted Jun 23, 2025

Informs front of house personnel of menu changes, specials and shortages. Documents, investigates, escalates and resolves employee or guest incidents.

Project Manager - Owners Rep

Company: Michael Page

Location: Chicago, IL

Posted Jun 24, 2025

Train and develop the project team. Our client is a design/build developer who specialize in K-12 and healthcare projects including but not limited to…

Registered Nurse Operations Coordinator Neurosurgery Full Time Days

Company: Northwestern Medicine

Location: Chicago, IL

Posted Jun 21, 2025

Current license as a Registered Professional Nurse or eligible in the State of Illinois. Supervise and direct the office’s front-line clinical and clerical…

Developer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Jun 24, 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…

Sales Consultant

Company: Zeigler Chrysler Jeep Dodge

Location: Downers Grove, IL

Posted Jun 24, 2025

Conduct cold calls to generate leads and build a strong customer base. In this role, you will be instrumental in driving sales and providing exceptional…

Shinola Retail Sales Associate - Oak Brook - PT

Company: Shinola- Retail

Location: Oak Brook, IL

Posted Jun 21, 2025

Show hospitality to your team members and guests alike. Connect guests with product meant to be lived in, well loved, and worn out.

Bindery/ Folder Operator

Company: Darwill, Inc.

Location: McCook, IL

Posted Jun 20, 2025

Quality Control steps completed accurately. High School degree or equivalent trade school training. Ability to identify inadequate machine operation and make…

Audit QC Director

Company: Porte Brown, LLC

Location: Elk Grove Village, IL

Posted Jun 23, 2025

BA/BS Degree in Accounting, Finance, or related field· CPA Certification · 8+ years of current public accounting experience· 2+ years of current public…

Digital Marketing Technology Specialist – Front-End Web (UX/Design Focus)

Company: Chamberlain Advisors LLC

Location: Chicago, IL

Posted Jun 24, 2025

The ideal candidate will have experience collaborating with creative and technical teams to build seamless, responsive user experiences and maintain a high…

District Sales Manager-Joint Care

Company: Fidia Pharma USA

Location: Chicago, IL

Posted Jun 23, 2025

Must hold a valid driver’s license and clean driving record. A bachelor’s degree in business, marketing, or a related field from an accredited college or…

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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