2026 Retail Entry-level Jobs in Chicago, IL
If you’re up to date on the latest trends in clothing, furniture, or other hot merchandise, you may be interested in entry-level jobs in retail. When most people think of jobs in retail, they think of manning cash registers or folding t-shirts, but there are actually many other types of retail jobs that offer upward mobility. In fact, some major corporations, such as Apple, offer training programs that start you with a lower-level job but that quickly help you to gain valuable skills that could qualify you for more prestigious positions. With Apple’s 24-month program, for example, qualified candidates are put to work at an Apple retail store, where they will try out various positions, take training classes, work with teams of other qualified individuals, and work directly with a knowledgeable mentor and supervisor known as a market leader. Those who successfully complete the program walk away with unique skills and the ability to apply for leadership positions at any of Apple’s many stores. Of course, not everyone can work for Apple, but there are plenty of other retail entry-level jobs that can be equally beneficial to you. Just be sure that you purposefully choose jobs that aren’t dead-end. Ask the hiring manager or supervisor what opportunities the position will offer you for personal and professional growth and advancement. You’d be surprised at just how many companies want to grow top employees from inside the organization. The pay for retail jobs and the exact job responsibilities will vary from one employer to the next, but your focus should be to find a job that will set the foundation for your future.
Mobile Associate, Retail Sales, Bilingual
SAP ABAP (Retail) Developer | 3 Months | Remote Role | Canada Client
General Manager of Retail - Eataly Chicago
Commercial Locksmith
Field Sales Representative - Chicago, IL
eCommerce Sales Manager-North America
Financial Crimes Manager
$150,000-$150,000 per year
Executive Underwriter - Property
Management Trainee - Schiller Park
Management Trainee - Palatine, IL
Management Trainee - Oak Park
Management Trainee - Lincoln Park
Management Trainee - Glenview
Management Trainee - Chicago
eCommerce Manager, National Accounts
CDL-A Dedicated TARGET Driver – Home Daily | 6-Day Workweek
CDL-A Local TARGET Driver –$1,550 Weekly + Home Daily
Executive Underwriter - Shared & Layered Property
Sales Representative
Sales Representative
Event Sales Assistant
Bread Baker (Full-Time) - Eataly Chicago
Customer Service Representative
Customer Service Representative
Automotive Service Manager
Pharmacy Tech Logan Square
Customer Service Representative
Manager, Pharmacy Accounting
$161,000-$171,000 per year
Experience Guide Sales Associate
Entry Level Marketing and Communications
Semi-Local Class A CDL Truck Driver
Class A CDL Driver
Warehouse Associate/Driver
Massage Therapist - Full Time and Part Time Available
Licensed Massage Therapist
CDL Driver
Semi-Local Class A CDL Driver - Dedicated Lane
Laundry Attendant
Real Estate Leasing Agent
Lube Technician
Lube Technician
HVAC/R Commercial Service Tech
Regional Sales Manager - A&D Architecture & Design
Sales Manager - Part Time - 30 Hrs a week
Customer Account Specialist
Certified Pilates Reformer Instructor
District Team Lead
$55,000-$65,000 per year
Civil Engineering Project Manager
Insurance Staff Position - State Farm Agent Team Member
Certified Pilates Apparatus Instructor
Fresh Market Manager (Full-Time) - Eataly Chicago
Customer Service Manager
Experience Guide (Front Desk Associate)
Medical Assistant- Part-Time - Nacogdoches
Outside Sales Representative - Commercial Cleaning
Licensed Esthetician Wax Specialist
Sales and Marketing Assistant
Sales Associate
Entry Level Inside Sales
$24-$24
Partner Inside Sales Representative (Remote)
Financial Services Representative – State Farm Agent Team Member
Business Development Representative-Consumer Packaged Goods
Dog Bather
Membership Specialist
Butcher
Bilingual - Operations & Billing Assistant
$41,600-$46,000 per year





















