Businesses for Sale in Chicago, IL

This Illinois-based NEMT company operates five days per week, transporting a diverse client base including Medicaid recipients, veterans, dialysis patients, and rehabilitation clients across the Chicago metro area and surrounding regions. The company is credentialed with all Illinois Medicaid managed care organizations and has established relationships serving federal transportation programs. It generates $285,000 in annual cash flow on a $900,000 asking price, with structural demand tailwinds driven by an aging population and expanding Medicaid coverage.

This nationwide first-and-final-mile logistics company operates a non-asset model with a fleet of 70 commercial trucks — 90% fully owned — and an established customer base that provides consistent cash flow across multiple U.S. markets. All existing company loans are structured to be satisfied at closing, delivering a clean balance sheet to the incoming owner. At a $1.189 million SDE on a $7 million asking price, the business offers an acquirer a scaled logistics platform with proven operational infrastructure and low capital expenditure requirements relative to asset-heavy transportation peers.

This year-round preschool and daycare in the Chicago metro area offers programs for infants through junior kindergarten age, with a play-based curriculum and dedicated teaching staff focused on early literacy, math, science, and social-emotional development. The pristine facility is ready for immediate operation and represents an ideal bolt-on acquisition for an existing childcare operator looking to add capacity in the market. SDE of approximately $143,000 on a $300,000 asking price reflects a stable and cash-generative operation in a sector with consistent demand.

This established dog training business in the Chicago metro area operates with proven training methods and a loyal client base seeking behavior modification and obedience programs. The facility generates consistent cash flow relative to its modest asking price, offering an accessible entry point for a dog trainer, pet industry operator, or enthusiast buyer. The business's track record and proven curriculum provide a replicable foundation that supports continued enrollment growth.

This upscale kitchen and bath remodeling contractor in the western Chicago suburbs has operated for multiple decades, specializing in complete design, demolition, and rebuild of kitchens and bathrooms with comprehensive services including cabinetry, countertops, flooring, plumbing, and lighting. The business has built a loyal repeat client base in an affluent suburban market and generates over $400K in annual SDE. At $1.1M on a sub-3x multiple, this is an attractive acquisition for a contractor or home services platform with the operational capacity to sustain and grow the business.

This Chicago-area yacht charter business transfers as a bundled acquisition including a luxury motor yacht, a commercial marina slip, and a non-replicable charter permit that the city no longer issues to new applicants. The established marketplace presence, customer database, and six years of operational history provide immediate revenue continuity for a buyer. The permit and slip combination creates a structural competitive moat that makes this opportunity impossible to recreate through new market entry.

This Chicago-area mental health practice has grown consistently since founding, reaching over $845,000 in 2025 revenue with strong profit margins and an established patient base supported by a comprehensive insurance panel including Medicare and Medicaid. High employee retention and a committed clinical team reduce transition risk and support continuity of care for existing patients. The practice's demonstrated growth trajectory and broad payer mix position it well for continued expansion under new ownership.

This metal roofing contractor and sheet metal distributor in the greater Chicago area combines contracting services with distribution capabilities, generating substantial discretionary earnings from a well-established position in the regional construction supply chain. The dual business model — providing both installation services and material distribution — creates multiple revenue streams and differentiated market positioning. Strong cash flow and a high-volume operation make this a compelling acquisition for a construction or distribution-focused buyer.

This well-established remodeling business has served the greater Chicago metro area for over two decades, providing comprehensive residential and commercial renovation services across both interior and exterior segments. With approximately $760K in annual cash flow on a $1.6M asking price, the business offers a strong earnings multiple with a proven operational history. The company's longstanding market presence and reputation for quality workmanship provide a durable competitive position for an acquiring operator.

This independent bread distribution route in the greater Chicago metro area delivers nationally recognized bakery brands to six grocery store accounts with a protected territory and generates approximately $102K in net annual income. The contracted distribution relationship with a major national bakery provides product supply stability and brand recognition, supporting a straightforward owner-operator business model. Company financing availability reduces the capital required at closing, improving accessibility for qualified buyers.