Retail Jobs in Chicago, IL
Retail jobs in Chicago are in strong demand across the Magnificent Mile, Wicker Park, and the Loop, with openings concentrated in fashion, luxury goods, home goods, and consumer electronics. Employers actively hiring include Logic, Macy's, and First Cash. See the openings below and apply to the ones that match your experience.
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At AIG, we are reimagining the way we help customers to manage risk. Join us as an Underwriter, Retail Property to play your part in that transformation. It’s an opportunity to grow your skills and experience as a valued member of the team.
Make your mark in Underwriting, Retail Property
AIG underwriting teams help to find insurance solutions in areas including Financial Lines, Property, Casualty, Specialty Lines, Cyber, Multinational Clients, and High Net Worth individuals. We are reimagining how we help customers to manage risk, transforming our operating model, and reshaping our role responsibilities and career pathways. The goal is to unlock the full potential in each colleague – empowering our people to grow as insurance professionals and add more value to our customers and AIG.
How you will create an impact
Reporting to the Zonal Underwriting Manager or Underwriting Lead, this role underwrites Retail Property Products under general supervision, issuing quote and policies while ensuring standards and compliance guidelines are met. These individuals will analyze information and have the opportunity to connect with clients and brokers.
- Underwriting a specific line of business within Retail Property
- Evaluating, prioritizing, and selecting submissions to be underwritten.
- Identifying risk exposures, special or common hazards, claims experience and appropriate controls.
- Analyzing claims and quantifying losses.
- Adhering to guidelines and underwriting discipline to minimize exposure and appropriately price risks.
- Ensuring underwriting files and services standards and compliance guidelines are adhered to on assigned accounts.
- Offering coverage, terms and conditions which generate a profit for the Company while meeting the needs of the customer.
- Capturing market intelligence and broker feedback on accounts.
- Begin demonstrating technical expertise with product(s) in the Financial Lines portfolio.
- Demonstrating strong business acumen, financial and analytical skills, and critical thinking skills which lead to confident decision making and judgment.
- Demonstrating success in negotiation and building collaborative relationships.
- Multi-tasking, prioritizing and time management skills
What you’ll need to succeed
- 1+ years of relevant professional experience. Commercial Insurance Company, Agency or Brokerage experience preferred.
- Bachelor’s degree from a four-year college or university.
- Demonstrated sales, marketing, and relationship building experience.
- Working knowledge of Retail Property products is preferred.
- Strong verbal and written communication skills.
- Ability to work in dynamic, rapidly changing environment, adapting to changing requirements and collaborating with a wide range of colleagues to quickly deliver solutions, especially regarding technical aspects.
- Comfort with financial statements, analytical tools and technology
For positions based in Illinois, the base salary range is $62,000-$82,500 and the position is eligible for a bonus in accordance with the terms of the applicable incentive plan. Your actual compensation will be dependent on your skills, experience, and qualifications. If your compensation expectations are above the posted range, we still encourage you to apply—your unique background matters to us. In addition, we’re proud to offer a range of competitive benefits, a summary of which can be viewed here: US Benefits Overview.”
At AIG, we value in-person collaboration as a vital part of our culture, which is why we ask our team members to be primarily in the office. This approach helps us work together effectively and create a supportive, connected environment for our team and clients alike.
Enjoy benefits that take care of what matters
At AIG, our people are our greatest asset. We know how important it is to protect and invest in what’s most important to you. That is why we created our Total Rewards Program, a comprehensive benefits package that extends beyond time spent at work to offer benefits focused on your health, wellbeing and financial security—as well as your professional development—to bring peace of mind to you and your family.
Reimagining insurance to make a bigger difference to the world
American International Group, Inc. (AIG) is a global leader in commercial and personal insurance solutions; we are one of the world’s most far-reaching property casualty networks. It is an exciting time to join us — across our operations, we are thinking in new and innovative ways to deliver ever-better solutions to our customers. At AIG, you can go further to support individuals, businesses, and communities, helping them to manage risk, respond to times of uncertainty and discover new potential. We invest in our largest asset, our people, through continuous learning and development, in a culture that celebrates everyone for who they are and what they want to become.
Welcome to a culture of inclusion
We’re committed to creating a culture that truly respects and celebrates each other’s talents, backgrounds, cultures, opinions and goals. We foster a culture of inclusion and belonging through learning, cultural awareness activities and Employee Resource Groups (ERGs). With global chapters, ERGs are a cornerstone for our culture of inclusion. The talent of our people is one of AIG’s greatest assets, and we are honored that our drive for positive change has been recognized by numerous recent awards and accreditations.
AIG provides equal opportunity to all qualified individuals regardless of race, color, religion, age, gender, gender expression, national origin, veteran status, disability or any other legally protected categories.
AIG is committed to working with and providing reasonable accommodations to job applicants and employees with disabilities. If you believe you need a reasonable accommodation, please send an email to candidatecare@aig.com.
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Who's Hiring



Top Industries Hiring
- Technology & Software
- Telecommunications
- Consulting & Professional Services
- Retail
- Manufacturing
Retail Jobs in Chicago: Frequently Asked Questions
How do I get a retail job in Chicago?
The fastest path is targeting Chicago's highest-volume hiring corridors: the Magnificent Mile for luxury and flagship stores, River North and Wicker Park for specialty and lifestyle brands, and Lincoln Park for home goods and boutique retail. Employers here favor candidates with demonstrated customer-facing experience, flexible weekend availability, and familiarity with POS systems. Applying directly to flagship locations and visiting in person during off-peak hours still gives Chicago applicants a real edge.
Which companies hire retails in Chicago?
Chicago retail roles are posted by Logic, Macy's, and First Cash and others right now, based on current listings on Migrate Mate as of July 2026. Chicago's retail employer mix includes national flagship operations anchored downtown, regional specialty chains, and independent boutiques concentrated in neighborhoods like Bucktown and the West Loop.
Are there remote retail jobs in Chicago?
Yes, though remote retail work is limited by nature since most roles involve in-store service, merchandising, or inventory. About 59% of retail openings tied to Chicago are remote or hybrid as of July 2026, reflecting positions in buying, e-commerce merchandising, and corporate retail operations. Chicago's concentration of regional headquarters means those desk-based retail roles are more available here than in smaller markets.
How can I get a retail job in Chicago with little or no experience?
The most realistic entry point is seasonal hiring at Chicago's flagship stores along the Magnificent Mile, where Nordstrom, Bloomingdale's, and large-format retailers routinely onboard first-time retail workers during peak seasons. Stockroom associate and cashier roles require no prior experience and often lead to full-time floor positions. Chicago's dense transit network also makes it practical to apply across multiple neighborhoods simultaneously, giving entry-level candidates a broader set of opportunities than most U.S. cities.
Which industries hire the most retails in Chicago?
The sectors hiring the most retails in Chicago are Technology & Software, Telecommunications, and Consulting & Professional Services, based on current listings on Migrate Mate as of July 2026. Chicago's status as a major fashion, financial, and tourism hub drives consistent retail demand across those sectors, supported by year-round foot traffic from both residents and convention visitors.
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