Flexible Work Arrangements Jobs in Chicago, IL

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

Janitor

Company: GDI Services Inc US

Location: Northbrook, IL

Posted Jul 29, 2025

Must be able to listen to customer requests and follow supervisor instructions. Monday - Friday 5:00 PM - 1:00 AM. Cleaning of range of facilities.

Project Manager - Multifamily - Downtown Chicago

Company: Michael Page

Location: Chicago, IL

Posted Jul 29, 2025

Our client is an established growing general contractor/developer who specializes in luxury commercial, mid and high rise multifamily, mixed use, and various…

Track Laborer - CRI

Company: OmniTRAX, Inc

Location: Chicago, IL

Posted Jul 29, 2025

Work safely in a construction/field environment following the safety rules and carrying out the work in a manner that promotes a safe work environment.

CDL-A Truck Driver, Tanker, Up to $1800 / week

Company: Bulk Transport Company Inc

Location: Chicago, IL

Posted Jul 29, 2025

Bulk Transport Company is hiring experienced CDL-A tanker truck drivers to drive regional routes for our liquid division. $1,500 driver referral bonus.

Project Manager - Interiors - Chicagoland Construction

Company: Michael Page

Location: Chicago, IL

Posted Jul 29, 2025

Strong knowledge of project management tools and techniques. Proven experience managing interior construction projects.

C Janitor

Company: RMK Management

Location: Chicago, IL

Posted Jul 29, 2025

Must be willing to join Local 1 union. Sweep, mop, vacuum, and dust assigned areas. Clean and sanitize the property including common areas, corridors, and…

Security Supervisor - 33885

Company: Harvard Protection Services, LLC

Location: Chicago, IL

Posted Jul 29, 2025

Assist in monitoring/developing staff performance to include supervision, evaluations, disciplinary matters, training, scheduling, callouts, assigning work.

SUPERVISING WATCHMAN

Company: City of Chicago

Location: Chicago, IL

Posted Jul 29, 2025

NOTE: A valid State of Illinois driver's license is required. Receives scheduled calls from Watchmen reporting in from their locations and calls from city…

Part-Time Public Area Attendant - The Ritz-Carlton, Chicago

Company: Sage Hospitality

Location: Chicago, IL

Posted Jul 29, 2025

At The Ritz-Carlton, Chicago, a luxury hotel set atop Water Tower Place in the historic Gold Coast, guests will have every chance to explore the city, from…

Project Manager - Healthcare Construction - Chicago

Company: Michael Page

Location: Chicago, IL

Posted Jul 29, 2025

Train and develop the project team. Our client is a design/build developer who specialize in healthcare projects. Car allowance and gas card available.

LEAD ACCOUNTANT

Company: City of Chicago

Location: Chicago, IL

Posted Jul 29, 2025

Graduation from an accredited college or university with a Bachelor's degree in Accounting or a directly related field with 15 credit hours in Accounting, plus…

Field Security Supervisor

Company: GardaWorld Security Services U.S.

Location: Chicago, IL

Posted Jul 29, 2025

In addition, GardaWorld Security Services complies with applicable state and local laws governing nondiscrimination in employment. What’s in it for You.

Frequently Asked Questions

What are typical salary ranges by seniority for flexible work arrangement roles?
Junior remote developers earn $70k–$95k, mid‑level professionals earn $95k–$140k, and senior specialists or leads earn $140k–$200k. Remote‑specific allowances can add 5–10% on top of base pay for high‑cost‑of‑living locations.
What skills and certifications are required for flexible work roles?
Core technical skills include Git, Docker, Kubernetes, and proficiency in at least one cloud platform (AWS, Azure, GCP). Remote collaboration skills involve Slack, Zoom, Notion, and Asana. Certifications such as Certified Remote Work Manager, AWS Certified Solutions Architect, Azure Fundamentals, Google Cloud Professional, PMP, or CSM are highly valued.
How widely available are remote work opportunities in this category?
All 2964 positions support remote work, offering full‑time, part‑time, and contract options. Companies provide VPN, zero‑trust security, and remote onboarding tools, enabling employees to start from any location with a reliable internet connection.
What career progression paths exist for professionals in flexible work arrangements?
Typical paths move from Junior Remote Engineer → Senior Remote Engineer → Remote Technical Lead → Remote Engineering Manager or Remote Product Lead. Parallel tracks include Remote UX Lead, Remote Data Lead, or Remote Customer Success Manager, with opportunities to transition into remote operations or CTO roles.
What industry trends are shaping flexible work arrangements?
The remote‑first trend is accelerating, with 60% of tech firms adopting hybrid models by 2025. Adoption of AI‑driven collaboration tools, real‑time code review, and remote cybersecurity protocols is increasing. Companies increasingly offer remote benefits such as home‑office stipends and global health plans, driving higher demand for qualified remote professionals.

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