Flexible Work Arrangements Jobs in Chicago, IL

74,530 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.

Specialty Sales (Style, Tech, Beauty) (T1888)

Company: Target

Location: Rosemont, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Style Consultant position with a starting hourly rate of $16.75 USD. The role involves providing excellent guest service, maintaining product availability, and creating an inviting shopping environment. Key responsibilities include greeting guests, understanding their needs, replenishing the sales floor, and executing visual merchandising. The position requires strong interest in apparel, effective communication, and the ability to work in a fast-paced environment. Target values teamwork, guest satisfaction, and offers comprehensive benefits.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T0868)

Company: Target

Location: Crestwood, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Guest Advocate role with a starting hourly rate of $16.75 USD. The position involves providing exceptional guest service, engaging with guests, and promoting Target's services and benefits. The role is dynamic, involving tasks like scanning, bagging, and maintaining a clean work area. Target values teamwork, communication, and a positive attitude. No two days are the same, with responsibilities ranging from assisting guests to managing returns and utilizing technology.

Risk Adjustment Program Manager

Company: CVS Health

Location: Chicago, IL

Posted Jan 23, 2025

CVS Health is seeking a Program Manager for their Risk Adjustment Retrospective Program, covering ACA, Medicare, MMP, and DSNP lines of business. The role involves provider/vendor/network outreach, production management, and reporting. The ideal candidate should have 5-7 years of work experience, strong analytical skills, and the ability to work in a fast-paced environment. Preferred qualifications include risk adjustment program experience within Medicare and a Bachelor's Degree. The pay range is $54,300.00 - $145,860.00, with additional benefits such as medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, education assistance, and more.

Retail Sales Associate - Northridge Center

Company: Gap Inc.

Location: Rock Island, IL

Posted Jan 23, 2025

Old Navy is a fashion retailer that aims to democratize style and make shopping enjoyable. They offer high-quality, affordable essentials for the whole family. The company, founded in 1994, values a fun, fast-paced work environment and community. The role involves providing excellent customer service, product expertise, and promoting brand loyalty. Benefits include a merchandise discount, competitive PTO, volunteer time, extensive 401(k), health insurance, and a commitment to diversity and inclusion.

Specialty Sales (Style, Tech, Beauty) (T1951)

Company: Target

Location: Decatur, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Style Consultant position with a starting hourly rate of $15.50 USD. The role involves providing excellent guest service, maintaining product availability, and creating an inviting shopping environment. Key responsibilities include greeting guests, understanding their needs, replenishing the sales floor, and executing visual merchandising. The position requires strong interest in apparel, effective communication, and the ability to work in a fast-paced environment. Target values teamwork, guest satisfaction, and offers comprehensive benefits.

Guest Advocate (Cashier), General Merchandise, Inbound (Stocking) (T3349)

Company: Target

Location: Chicago, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is hiring for a Small Format Team Member role. The position involves providing exceptional guest service, managing store operations, and ensuring product availability. Responsibilities include greeting guests, assisting with purchases, maintaining store presentation, and executing inventory tasks. The role requires a welcoming attitude, ability to work in a fast-paced environment, and physical capabilities like lifting and climbing. Target offers comprehensive benefits and opportunities for career growth.

Staff Engineer - Android

Company: CVS Health

Location: Buffalo Grove, IL

Posted Jan 23, 2025

CVS Health is seeking a Staff Engineer - Android to work on the customer-facing Flagship CVS app. The role involves advancing architecture and mobile product, partnering with cross-functional teams, and mentoring team members. The ideal candidate should have 7+ years of software development experience, with at least 7+ years in designing/developing Android mobile applications. They should be a subject matter expert in software engineering best practices and the Health and e-Commerce domain. Responsibilities include developing Android code, improving CI/CD infrastructure, collaborating on solutions to reduce cost and time to market, and providing technical guidance to fellow engineers.

Guest Advocate (Cashier or Front of Store Attendant/Cart Attendant) (T0928)

Company: Target

Location: Niles, IL

Posted Jan 23, 2025

Target, a Fortune 50 company, is offering a Guest Advocate role with a starting hourly rate of $17.00 USD. The role involves providing exceptional guest service, engaging with guests, and promoting Target's services and benefits. The job requires strong communication skills, a welcoming attitude, and the ability to handle multiple tasks in a fast-paced environment. Target values teamwork, guest satisfaction, and continuous learning.

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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