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Businesses for Sale in Chicago

Rejigg has 46+ active listings within 60 miles, spanning Illinois, Indiana and Wisconsin.

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8

New This Month

46

Active Listings

$1.1M

Median Asking Price

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Businesses in the Chicago Metro Area

Showing 25 of 46 listings within 60 miles of Chicago

Residential Roofing & Exteriors Contractor

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.
Price$1.8M
Revenue$2M
SDE$251.7K

HVAC / Electrical Services Business

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.
Price$660K
Revenue$452.3K
SDE$79.5K

Business IT Support Service

HIPAA-certified managed service provider generating $15k in monthly recurring revenue from medical clients, with a hospital referral partnership delivering two to three new client opportunities per year at zero marketing cost.
Price$1.2M
Revenue$303K
EBITDA$210.5K

Digital Marketing Agency

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.
Price$2M
Revenue$720.5K
EBITDA$326.3K

Holistic Healing and Massage Therapy Center

A healing collective operating as a lean direct-to-consumer brand with over 65% EBITDA margins and minimal owner involvement.
Price$75K
Revenue$82.7K
SDE$55.2K

Financial Healthcare Staffing Specialists

Over 35 years of client relationships in financial services and nonclinical healthcare staffing, with the largest client expanding from seasonal to year-round work under private equity ownership.
Price$950K
Revenue$2.8M
SDE$294.6K

Suburban Auto Repair Franchise

A 13-location auto repair group across suburban Illinois generating over $21M in combined annual revenue, with a franchise structure expected to dissolve and eliminate ongoing fees, creating a rare multi-shop acquisition window.
Price$1.2M
Revenue$1.8M
SDE$213.7K

Full-Service Commercial Print Shop

Over 40 years of commercial printing and fulfillment operations with 80% recurring clients, a 15-person team running independently, and negotiated shipping margins that drive outsized fulfillment profit.
Price$3M
Revenue$3.5M
EBITDA$700K

Managed IT Services & Technology Consulting Firm

Nearly thirty-year-old managed services provider generating $3.1M in revenue with a proprietary SaaS monitoring tool, owner-absentee operations, and a leadership team that runs day-to-day independently.
Price$3.8M
Revenue$3.1M
SDE$828.5K

Intermodal Trucking Business

Local intermodal trucking agency generating $1.5M in 2025 revenue with a recurring customer base of commercial freight brokers and demonstrated capacity to scale past $3.4M.
Price$750K
Revenue$1.5M
SDE$224.7K

Educational Tutorial Service Franchise

Franchise tutoring center with nearly ten years of operations, $200k in prepaid unearned revenue, and award-winning recognition from the franchisor, serving three school districts from a single location in Southern California.
Price$360K
Revenue$708.2K
SDE$133.3K

Immersive Urban Art Experiences

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.
Price$350K
Revenue$805.7K
EBITDA$47K

Specialized Product Design Firm

A product development consultancy with over 30 years of market presence, Class I and Class II medical device experience, and a portfolio spanning research, industrial design, UX/UI, and mechanical engineering. The business generated $763k in 2025 revenue with a lean three-person team.
Price$290.5K
Revenue$763.2K
SDE$153.7K

Manufacturing Solutions Business

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.
Price-
Revenue$5.3M
SDE$459K

Telecom Permitting & Zoning Consultancy

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.
Price$2.2M
Revenue$864.4K
SDE$482.3K

Latino Mental Health Marketplace

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.
Price$3.3M
Revenue$1.1M
EBITDA($340K)

Nonprofit Fundraising Strategy Consultancy

Nonprofit fundraising consultancy with over forty years of brand equity, a 300+ client track record, and retainer-based revenue driven almost entirely by referrals.
Price-
Revenue$735K
EBITDA$422.5K

Waste Management Business

Waste industry service company operating across nine Midwestern states with $5.1M in 2025 revenue, serving major national haulers at roughly 35% of their internal costs for compactor and container work.
Price-
Revenue$5.1M
SDE$346.9K

Plastering Business

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.
Price$10.5M
Revenue$12.7M
EBITDA($500K)

Precision CNC Machine Distributor

Exclusive US distribution rights for a European precision CNC machine manufacturer, with approximately 1,000 active customers and thousands of installed machines generating recurring parts and service revenue across North America.
Price$150K
Revenue$482.2K
SDE$33.5K

Technical Content Creation Agency

Technical content marketing agency building developer-focused content engines for B2B software companies, generating $1.3M in annual revenue through a fully remote, contractor-based model with minimal owner involvement in day-to-day production.
Price$800K
Revenue$1.2M
SDE$259.6K

Mail Sorting / Handling 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.
Price-
Revenue$3M
EBITDA$303K

Custom Manufacturing Business

Engineering-driven custom automation and test equipment manufacturer with over twenty years of history, in-house machining capabilities, and $3M in 2025 revenue.
Price$294K
Revenue$3M
SDE$116.6K

IT Infrastructure Company

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%.
Price$10M
Revenue$1.5M
EBITDA$350K

Mexican Restaurant

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.
Price-
Revenue$1.7M
SDE$148.8K
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FAQ

Buying a Business in Chicago

What types of businesses are for sale in Chicago?

Rejigg lists a variety of businesses for sale in the Chicago metro area, including professional services, manufacturing, software companies, healthcare businesses, retail operations, construction companies, and more. Each listing is individually sourced and vetted by our team to ensure quality opportunities.

How do I buy a business in Chicago?

To buy a business in Chicago through Rejigg: 1) Create a free account and complete your buyer profile, 2) Browse listings and filter by industry, price range, and other criteria, 3) Request an introduction to connect directly with the business owner, 4) Schedule calls and conduct due diligence through our platform. We facilitate direct buyer-seller communication without expensive broker fees.

What is the typical price range for businesses in Chicago?

Businesses for sale in the Chicago area range from under $500,000 to over $10 million. Price depends on factors like annual revenue, profitability (EBITDA/SDE), industry, growth potential, and asset value. Use our filters to find businesses within your budget and financing capabilities.

Can I connect directly with business owners in Chicago?

Yes! Rejigg enables direct communication between buyers and sellers. Unlike traditional business brokers who act as intermediaries, we facilitate introductions so you can have authentic conversations with business owners about their companies, ask detailed questions, and build rapport before making an offer.

Are the businesses on Rejigg vetted?

Yes, all businesses listed on Rejigg are individually sourced and vetted by our team. We verify financial information, confirm owner motivation to sell, and ensure the opportunity is legitimate before listing. This means you're connecting with qualified, real opportunities rather than wasting time on tire-kickers or fraudulent listings.

What financing options are available for buying a business in Chicago?

Common financing options for acquiring businesses include SBA 7(a) loans (up to $5 million with favorable terms), conventional bank loans, seller financing (where the seller provides a loan), investor equity, or a combination. Rejigg provides tools like our SBA Calculator to help you understand your financing options. Many successful acquisitions use 10-20% buyer equity with the remainder financed.