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.

Experienced Fine Jewelry Sales Professional

Company: Sidney Garber

Location: Chicago, IL

Posted May 20, 2025

Manage relationships with established clients, new sales leads and prospects through the use of detailed clienteling and CRM tools.

Plumbing and Sewer Technician

Company: Do Right Rooter Drain Specialists

Location: Bridgeview, IL

Posted May 15, 2025

Valid driver’s license and a good driving record. Collaborate with general contractors, electricians, and other construction professionals.

Registered Nurse (RN)

Company: Team Select Home Care

Location: Oak Brook, IL

Posted May 15, 2025

Maintains a current CPR certification. Working with pediatric/adult patients with g-tube, trach, and/or ventilator. Medical, Dental, and Vision insurance.

Special Education Teacher

Company: The Menta Education Group

Location: Chicago, IL

Posted May 21, 2025

IL PEL (Professional Educator's License; out-of-state applicants will need to apply for IL certification) with LBS1 Certification or Other Teacher Certification…

Registered Nurse RN Home Health

Company: Elara Caring

Location: Chicago, IL

Posted May 23, 2025

Must have a dependable vehicle, valid driver’s license, and current auto insurance in accordance with state laws. 401(K) with employer match.

Part Time Sales Associate - BOSS Store, Chicago

Company: Hugo Boss

Location: Chicago, IL

Posted May 15, 2025

Utilize effective communication skills in delivering exceptional service to customers, driving business with the merchant group and general problem solving.

Service Reliability Project Lead

Company: Progress Rail

Location: La Grange, IL

Posted May 21, 2025

The Service Reliability Project Lead is responsible for understanding in-service product failure data, identifying product performance trends, driving…

Senior Finance Analyst

Company: Expedia Group

Location: Chicago, IL

Posted May 21, 2025

Support, develop, and implement improved processes and controls to enable sustainable, profitable scaling of the PLS business.

RETAIL SALES ASSOCIATE

Company: Ashley

Location: Bolingbrook, IL

Posted May 21, 2025

Maintain a welcoming, professional, visible presence at the front desk; engage with guests, ensuring they are always treated in a cordial, respectful manner…

Machine Operator | 3rd Shift

Company: Verstela

Location: Northlake, IL

Posted May 24, 2025

Maintenance & Troubleshooting: Perform routine maintenance on equipment, troubleshoot issues, and assist in basic repairs to minimize downtime.

Clinical Analyst

Company: JACKSON PARK HOSPITAL AND MEDICAL CENTER

Location: Chicago, IL

Posted May 16, 2025

Assist in the development and implementation of new digital tools and technologies to improve patient outcomes. Associates Degree Minimum, Bachelors preferred.

Facilities Painter

Company: The Resurrection Project

Location: Chicago, IL

Posted May 22, 2025

Access to a car, valid driver's license, and ability to travel within the metropolitan area and out of state. Access to a motor vehicle, valid driver’s license,…

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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