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.

Project Manager- Chicago Construction

Company: Michael Page

Location: Chicago, IL

Posted Jul 09, 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…

CHICAGO SOUTH LOOP ELECTRICIAN

Company: State of Illinois

Location: Chicago, IL

Posted Jul 09, 2025

Requires a valid driver’s license and the ability to travel to various sites/facilities. Under general supervision, receiving day-to-day guidance from the Chief…

Overnight Security Guard

Company: KH Security Inc.

Location: Chicago, IL

Posted Jul 08, 2025

*Must have your own vehicle. *Must have a valid Perc Card and 20 hours training certificate*. KH Security Inc. provides best in class security services for…

Project Manager - Multifamily Projects - Chicago

Company: Michael Page

Location: Chicago, IL

Posted Jul 08, 2025

Ability to hire, train, and develop a team of Project Managers. Car allowance and gas compensation included. Experience on mid to large size projects.

Project Manager - Multifamily Developer

Company: Michael Page

Location: Chicago, IL

Posted Jul 08, 2025

The Project Manager is responsible for scheduling, oversight of construction and communication with project team. Bonus per project (up to 12%).

Marketing Graphic Designer

Company: Oak Park Park District

Location: Oak Park, IL

Posted Jul 08, 2025

Associate or bachelor’s degree in graphic design, Communications, Marketing, Electronic Media/Fine Arts, Digital Media, or related field.

Culinary Director

Company: Soul & Smoke

Location: Chicago, IL

Posted Jul 08, 2025

Driver’s license is strongly preferred. This role partners with the Chef, office team, and kitchen staff to maintain high standards while driving efficiency and…

Employee Service Center Representative - Chicago

Company: MSG Entertainment Holdings, LLC

Location: Chicago, IL

Posted Jul 08, 2025

Act as the primary point of contact for employee inquiries, handling communications via phone calls, in person interactions, and ticketing system, while…

Local Sous Chef

Company: HSG

Location: Elmhurst, IL

Posted Jul 08, 2025

Monitor food quality, presentation, and portion control to meet guest expectations. Assist with training new kitchen staff on kitchen procedures, safety…

Painter

Company: Potbelly

Location: Chicago, IL

Posted Jul 08, 2025

Travel occasionally for repairs, installations, or deliveries. Competitive pay with performance-based annual raises! FSA and HSA with Employer Contribution.

Staff Accountant

Company: Windfall Group

Location: Oak Brook, IL

Posted Jul 08, 2025

Associate’s or Bachelor’s degree in Accounting, Finance, or related field. Work with property managers and construction teams to ensure invoice accuracy and…

Insulation Technician-Independent Contractor

Company: Green Attic Insulation

Location: Mount Prospect, IL

Posted Jul 08, 2025

Reliable transportation and valid driver's license. Operate and maintain insulation equipment and tools. Familiarity with tools and machinery used in insulation…

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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