Businesses for Sale in Chicago.

Third-generation residential roofing operation with over sixty years of brand equity generating $2M to $2.5M in baseline revenue with two operators and zero employee overhead.

Referral-driven HVAC and electrical contractor serving the Chicago suburbs with 60% commercial revenue, a 6,500-customer database, and services spanning home automation, server room cooling, and radiant heating.

Fully remote digital marketing agency with 90%+ client retention over 24 months, 30-60% margins, and $720k revenue in 2025 generated entirely without spending on its own brand marketing.

A healing collective operating as a lean direct-to-consumer brand with over 65% EBITDA margins and minimal owner involvement.

Professional staffing agency with over thirty-five years of operating history, 53% average markups on contingent placements, and client relationships spanning up to thirty years across financial services and nonclinical healthcare.

Four-bay auto repair shop generating $1.8M in revenue with a six-year manager running daily operations independently, a lease locked through 2032, and franchise royalty costs expected to be eliminated.

Over forty-five years of recurring client relationships and in-house production capabilities that 99% of competitors cannot match, generating $3.5M in revenue with the business operating independently of the owner for over six years.

Nearly 30-year-old managed services provider generating $3.1M in revenue with a proprietary SaaS monitoring tool, a leadership team operating independently for years, and zero owner involvement in day-to-day operations.

Drayage and container transport operation with eight drivers, established broker relationships spanning over eight years, and $1.8M in 2026 revenue on an asset-light owner-operator model.

Immersive street art experience business operating two studios across the Midwest and Southeast, with revenue nearly doubling from $391k in 2021 to $825k in 2026 and margins now inflecting sharply upward.

A product development consultancy with over thirty years of continuous operation, award-winning designs, and capabilities spanning ethnographic research through design-for-manufacturing across medical devices, consumer electronics, and commercial equipment.

Manufacturing solutions provider specializing in assembly and automation processes for automotive, appliance, construction, and consumer goods sectors with a newly secured OEM contract adding $1.35M at 40% gross margins.

Permit consulting firm operating across 25 states with multi-year MSAs from the three largest wireless tower owners, generating over $480k in SDE on a two-person team.

Tech-enabled mental healthcare marketplace connecting Spanish speakers in the U.S. with licensed providers in Latin America delivering 2,000 sessions per month at 50% gross margins, addressing a supply gap where 13% of U.S. households speak Spanish but only 5% of providers offer services in the language.

Nonprofit fundraising consultancy with over forty years of brand equity, a 300+ client track record, and retainer-based revenue driven almost entirely by referrals.

Full-service compactor and baler operation providing 24/7 emergency service across eight Midwestern states, with nearly 20 years of organic growth driven entirely by reputation and zero dedicated sales effort.

Commercial plastering contractor with $17M contracted 2026 pipeline, offering acoustical plaster, cement plaster, cultured stone, and specialized finishes in a niche market where labor scarcity supports pricing power.

Exclusive US distribution and service rights for a legacy CNC machine line with thousands of installed units, a phone number stamped on every machine since the 1950s, and no competition for parts or service.

Mail presorting services operation approaching $3M in revenue with SDE growth of 47% from 2023 to 2025, driven by a leaner cost structure and steady client demand across Illinois.

Engineering-driven custom automation and test equipment manufacturer with over twenty years of history, in-house machining capabilities, and $3M in 2025 revenue.

Data communications infrastructure firm with over 20 national partner contracts, a fully remote workforce of approximately 20 engineers across eight states, and 25-30% margins roughly double the industry standard of 15-20%.

Mexican restaurant and tequila bar operating across multiple locations in Illinois, generating $1.7M in annual revenue with consistent performance and additional catering and event revenue streams.

Finance and accounting executive search firm with 70%-plus placement rate and exclusive client relationships spanning over five years, delivering 60% margins on $500k revenue.

A licensed low-voltage security business in the Chicago metro area on pace for record revenue in 2026, with recurring monitoring contracts, a deep base of property managers and business owners, and multiple service lines including alarms, access control, fire alarms, and camera systems.

Over 200,000 books sold across nine languages generate a near-zero cost of sales pipeline for a quantitative consulting firm that operates with close to 50% margins and requires less than half a day per week from the owner.