Flexible Work Arrangements Jobs in Chicago, IL

74,517 open positions · Updated daily

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.

Entry Level Marketing & Sales Associate

Company: Penguin Promo Partners

Location: Bridgeview, IL

Posted Aug 07, 2025

In-office collaboration with retail field deployment. No prior sales experience is required—our hands-on training program equips you with the skills to succeed.

Community Relations Manager

Company: Mather Headquarters

Location: Evanston, IL

Posted Aug 08, 2025

Support program development and implementation with partners and Community Initiatives team. At least five years professional experience in Not For Profit,…

Executive Chef - City Venues

Company: DineAmic Hospitality

Location: Chicago, IL

Posted Aug 08, 2025

Conduct ongoing research and continuously develop menu items with respect to changing seasons, guest feedback, product cost and availability, and other factors.

Client Success Coordinator

Company: CST Academy

Location: Chicago, IL

Posted Aug 07, 2025

*Sales Support:* Respond to inquiries, provide detailed information about our services, and convert leads into active clients.

Manual Turning (CNC Machining)

Company: BROADWIND INC. & SUBSIDIARIES

Location: Cicero, IL

Posted Aug 07, 2025

Sitting or standing for periods of time; walking, climbing, crawling, bending, twisting or stooping; may be exposed to noise, dust, fumes, vibrations if…

Staff Accountant For Fine Dining Restaurant Group

Company: Le Colonial and Le Bilboquet Fine Dining Restaurant Group

Location: Chicago, IL

Posted Aug 08, 2025

Sales, Payroll and Cash Flow Analysis. Some Accounts Payable and check disbursements. The ideal candidate will be extremely well organized, have excellent…

The North Face: Sales Associate - Chicago

Company: The North Face

Location: Chicago, IL

Posted Aug 08, 2025

Operate office equipment and technology (i.e., computers, tablets, phones, copier, etc.). As a Sales Associate you will be the face of the brand to our retail…

QA Analyst, BI

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Aug 07, 2025

Familiarity with web development concepts (e.g., React, responsive design), APIs, and relevant testing tools is beneficial.

Porter

Company: Puttery

Location: Chicago, IL

Posted Aug 08, 2025

The role of a Porter is to keep the venue clean and organized for our guests. In addition, all staff is expected to create and maintain an inviting atmosphere…

Seasonal Security Officer - DoubleTree by Hilton Hotel Chicago Magnificent Mile

Company: Hilton

Location: Chicago, IL

Posted Aug 08, 2025

As a Security Officer, you would be responsible for ensuring the safety of guests and team members and the security of the hotel and property in the hotel's…

Carpenter

Company: Kiwi Carpenters LTD

Location: Oak Park, IL

Posted Aug 07, 2025

Must have a valid drivers license and the legal right to work in the United States; Kiwi Carpenters is unable to provide sponsorship for employment visas.

Manager, Data Science

Company: PayPal

Location: Chicago, IL

Posted Aug 08, 2025

We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account…

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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