Find Small Businesses for Sale in Cook County, IL on DealStream

Discover top small businesses for sale in Cook County, Illinois on DealStream—your go-to marketplace for buying a turnkey venture in Chicago, Evanston, Oak Park and beyond. Our curated listings span restaurants, retail shops, service providers and more, complete with detailed financials and direct seller contact. Start your search now to find and acquire the perfect Cook County small business today!

All Matching Deals

Established Commercial Screen Printing Business
Chicago, IL

This well-established screen printing company was founded by industry professionals who recognized the growing demand for high-quality printing services. With a focus on communication, reliability, honesty, and competitive service, it has earned a strong reputation for excellence. The company has successfully...

$1,167,605
Cash Flow: $343,413
Details
Established Trucking Logistics Company For Sale
Cook County, IL

Well-managed Midwest transportation business that transports products for a variety of industries. Their fleet includes 16 trucks, 14 trailers, and 10 experienced drivers. Trucks and trailers are valued at approximately $967,000 and will be paid off in full at closing. The seller will stay...

$1,500,000
Cash Flow: $570,000
Details
Cook County, IL

Founded in 1988, this company is a highly established, full-service laser marking and laser engraving contract job shop serving manufacturers that require permanent, high-precision part identification. The business has grown from a single-laser operation into a technologically advanced platform operating...

$1,500,000
Cash Flow: $299,299
Details
High-Visibility Smoke & Vape Store Ideal for Portf
Cook County, IL

This is an established smoke and vape retail business operating from a highly visible storefront along a busy commercial corridor. The location benefits from strong traffic exposure, easy ingress and egress, and ample parking, making it well positioned for steady demand. The business offers a broad...

$1,100,000
Cash Flow: $211,715
Details
Established Breakfast & Lunch Restaurant with Real
Cook County, IL

This is a long-standing, full-service breakfast and lunch restaurant located in a high-traffic corridor on the south side of Chicagoland. The business is known for its welcoming atmosphere, consistent operations, and strong customer loyalty built over many years. Sales exceed $1.3M annually with a simple,...

$1,750,000
Cash Flow: $115,169
Details
Well Established Orthopedic Practice
Cook County, IL

Well established and nicely managed orthopedic practice operating in the same location for over 30 years. Located in an easily accessible Chicago suburb, this practice treats various orthopedic conditions such as sprains, strains, fractures, and chronic conditions like arthritis and bursitis. 19...

$1,900,000
Cash Flow: $578,813
Details
Confidential Turnkey HVAC Supply With Real Estate
Cook County, IL

This is a confidential sale of a turnkey HVAC supply, equipment, and scratch-and-dent distribution company serving the Southwest Suburbs of Chicago. The business generates approximately $573,397 in annual revenue with strong margins across residential and commercial HVAC categories. Normalized SDE is...

$1,500,000
Cash Flow: $175,917
Details
Cook County, IL

Unique investment opportunity six established, profitable stores, with expansion potential through the rights to build 2 additional locations. Facials in 30 Minutes. A rare opportunity to own an exclusive modern facial bar revolutionizing skincare with efficient, results-driven treatments in just 30...

$1,500,000
Cash Flow: $284,531
Details
Established Internal Medicine Practice in Chicago
Chicago, IL

For Sale: Established Internal Medicine Practice – Northwest Suburbs of Chicago Exceptional opportunity to acquire thriving internal medicine practice with deep roots in the local community and significant growth potential. This well-known and respected practice consistently generates average annual...

$1,400,000
Details
Chicago, IL

Location: South Side Chicago Price: $1.2 Million (All Cash) Property purchase option available Business Highlights: • Inside sales over $120,000 per month • Fuel sales: 20,000 gallons per month • Large store with room for expansion • Located in a high-traffic, active neighborhood • Staffed...

$1,200,000
Details
Cook County, IL

Extremely profitable cabinet and countertop distribution business. Has long term builder and GC relationships as well as fiercely loyal residential quick pay clientele. Significant additional revenue streams available. Owner operated, prime for scaling with all tenured vendor relationships in place....

$1,500,000
Cash Flow: $120,600
Details
Countertop Fabricator & Installer
Chicago, IL

Own a thriving business in the heart of Illinois! A well-established countertop fabrication and installation company with a stellar reputation for quality craftsmanship, customer service, and timely project completion. Servicing residential, commercial, and custom builder markets, this is a turnkey...

$4,500,000
Cash Flow: $815,000
Details
Venue Business For Sale /  Price Improved
Chicago, IL

Extraordinary Investment Opportunity with Breathtaking Views! Discover the allure of acquiring a distinguished event venue nestled in a serene riverside community, strategically positioned within a lively downtown locale. This remarkable establishment caters to an array of events, from opulent weddings...

$1,600,000
Details
Heart-Healthy Shortening  since 1952.
Chicago, IL

Premium Heart-healthy, clean label and soybean-based Superior functionality and performance Cost-effective, U.S.-made shortening Grown in the USA Kosher, Halal & Non-GMO

$2,500,000
Cash Flow: $500,000
Details
Profitable & Independent Insurance Agency for Sale
Cook County, IL

Wildly successful independent insurance agency for sale with minimum 35%+ year over year growth since 2020 focusing on mainly personal auto insurance AND a separate revenue stream (i.e. car registration that makes up 46% of revenue) located next to a DMV. We repeat that almost 50% of the revenue of...

$1,150,000
Cash Flow: $428,734
Details
Kitchen Cabinet Manufacturing, Sales, Dist.
Cook County, IL

Cabinet Sales, Assembly & Distribution (1/3rd Seller Financing!!) This company does over $1.7M in annual sales with a robust bottom line and cash flow. There is one showcase gallery to sell this custom European product and/or more affordable options for consumers and commercial accounts. Over $1M+...

$1,500,000
Cash Flow: $269,500
Details

Tips for Buying A Business

Perform Thorough Due Diligence

Before committing to a business purchase, conduct a comprehensive due diligence process. Review all financial statements, tax returns, customer contracts, and legal documents to ensure there are no hidden liabilities or risks. Interview key employees and suppliers to get a sense of operational stability and reputation. This deep dive will provide a clear understanding of the business's true performance and highlight any potential problem areas that need to be addressed prior to closing.

Understand the Industry and Market

Take time to fully understand the industry in which the business operates. Research market trends, potential competitors, and current challenges facing the sector. Analyze what sets this business apart and whether its value proposition will remain strong in the coming years. A thorough grasp of the market context will help you assess growth potential and make an informed decision about the long-term viability of your investment.

Negotiate the Best Deal

Approach negotiations with a clear understanding of both your goals and the seller’s motivations. Don’t be afraid to ask for favorable terms, such as seller financing, a transition period with the current owner, or contingencies based on future performance. Working with experienced advisors, such as business brokers, accountants, and attorneys, will strengthen your negotiating position and help structure a deal that minimizes risk while positioning you for success after the purchase.