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.

Management & Sales Training Program

Company:

Location: West Dundee, IL

Posted Feb 06, 2025

Shift Supervisor Trainee

Company: CVS Health

Location: Atlanta, IL

Posted Feb 06, 2025

Grant Proposal Manager

Company: SGA YOUTH & FAMILY SERVICES NFP

Location: Chicago, IL

Posted Feb 05, 2025

Prepare and submit funding applications/reapplications/proposals to local, state and federal government agencies. Excellent writing skills are necessary.

Senior Financial Audit Consultant

Company:

Location: O'Fallon, IL

Posted Feb 06, 2025

Back Office US Team Lead

Company: RWE Clean Energy

Location: Chicago, IL

Posted Feb 06, 2025

Warehouse Worker - Woodridge, IL

Company: Henry Schein

Location: Bolingbrook, IL

Posted Feb 04, 2025

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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