Businesses for Sale in Chicago

Rejigg has 33+ active listings within 60 miles, spanning Illinois, Indiana and Wisconsin.

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4

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33

Active Listings

$1.6M

Median Asking Price

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Businesses in the Chicago Metro Area

Showing 25 of 33 listings within 60 miles of Chicago

Roofing Business

Third-generation roofing, siding, and gutter services provider serving the greater Chicago metropolitan area with a lean, subcontractor-based model focused primarily on residential projects and recurring HOA contracts
Price$1.8M
Revenue$2M
SDE$401.2K

HVAC / Electrical Services Business

Provides residential and commercial HVAC and electrical services across Illinois, including installation, repair, maintenance, home automation, security systems, server room cooling, and radiant heating, with approximately 60% commercial workload and a strong referral-based customer base
Price$660K
Revenue$1.5M
SDE$348.3K

Regional Trucking & Logistics Company

Operates a fleet of approximately 800 trucks and 2,000+ trailers providing nationwide transportation solutions including dry van, refrigerated, hazmat, flatbed, and step deck shipments across a diversified customer base of 200+ active clients with a mix of contract-dedicated and spot market freight
Price$45M
Revenue$135.8M
SDE$10.3M

Business IT Support Service

Hipaa-certified managed service provider offering IT support, monitoring, backup and disaster recovery, web design, and consulting services primarily for medical clients in northwest Indiana, with recurring revenue from managed support contracts and referral-based client acquisition through a regional hospital partnership
Price$1.2M
Revenue$303K
EBITDA$210.5K

Digital Marketing Agency

Fully remote agency offering web development, seo, search engine marketing, social media, email marketing, and a proprietary linkedin business development program to small and mid-size businesses across 39 states and three countries
Price$2M
Revenue$494.2K
EBITDA$285.1K

Holistic Healing and Massage Therapy Center

Offers massage therapy, bodywork, energy healing, and one-on-one mentoring to foster holistic healing and personal growth.
Price$75K
Revenue$98.3K
SDE$60.4K

Auto Repair Shop

Franchised four-bay auto repair and maintenance shop serving cars, SUVs, minivans, and light trucks in suburban Chicago for approximately five years
Price$1.2M
Revenue$1.8M
SDE$205.7K

Chemical Cleaning Supplier

Wholesale janitorial supply distributor offering cleaning chemicals, wiping paper products, mops, buckets, cleaning equipment, and custom entrance matting to education, healthcare, municipal, hospitality, and commercial clients
Price$1.5M
Revenue$3.5M
SDE$400K

Commercial Printing and Mailing Business

G7 certified full-service commercial printer offering offset and digital printing, bindery, specialty finishing, perfect-bound book production, UV coating, and in-house mailing solutions from a 27,000 square foot facility serving the greater Chicago area
Price$3M
Revenue$3.5M
EBITDA$700K

Managed IT Services & Technology Consulting Firm

Provides managed it, cybersecurity, cloud hosting, and technology consulting services along with a proprietary saas monitoring tool to small and mid-sized businesses across diverse industries in the chicago metro area and beyond
Price$3.8M
Revenue$3.2M
SDE$537.6K

Intermodal Trucking Business

Operates a local intermodal trucking agency serving commercial freight brokers with transactional, order-by-order revenue from a highly recurring customer base
Price$750K
Revenue$1.5M
SDE$224.7K

Educational Tutorial Service Franchise

Provides individualized tutoring and standardized test preparation programs for K–12 students through in-center, online, and hybrid formats, with additional revenue from contract-based and grant-funded institutional partnerships with schools, districts, and community organizations
Price$360K
Revenue$708.2K
SDE$142.6K

Midwest Urban Event Collective

Offers immersive street art workshops, neon art sessions, and guided tours at studios in chicago and atlanta, plus an online shop selling branded merchandise and artist collaborations
Price$350K
Revenue$805.7K
EBITDA$43K

Specialized Product Design Firm

Offers strategic product development services including research, industrial design, UX/UI, mechanical engineering, CAD modeling, 3D prototyping, and design-for-manufacturing across industries such as consumer electronics, healthcare, home products, and commercial equipment
Price$290.5K
Revenue$763.2K
SDE$111.4K

Injection Molding Business

Full-service toolmaking business specializing in design and manufacture of die cast dies, plastic injection molds, and prototype tooling, offering comprehensive lifecycle services including engineering, reverse engineering, die refurbishing, and repair for automotive OEMs, tier 1 suppliers, and industrial manufacturers under an ISO 9001:2015-certified quality system
Price$9.6M
Revenue$11.1M
SDE$739.8K

Manufacturing Solutions Business

Specializes in assembly and automation processes for automotive, appliance, construction, and consumer goods industries, offering services including drilling and tapping, part dotting and painting, packaging, sorting and inspection, and distribution
Price-
Revenue$5.3M
SDE$459K

Construction Consulting Company

Specializes in building permit expediting, zoning approvals, and wireless telecom site acquisition services across approximately twenty-five states, serving large wireless tower owners, telecom carriers, developers, and architects through a fully remote operation
Price$2.2M
Revenue$876.9K
SDE$496.4K

Tech-Enabled Mental Healthcare Marketplace

Connects spanish-speaking patients in the u.s. with licensed psychologists and emotional support providers based in latin america through an online marketplace offering individual and couples therapy sessions
Price$3.3M
Revenue$917.3K
EBITDA-$103K

Consulting Firm for Nonprofit Organizations

Provides fundraising, capital campaign, board development, strategic planning, and organizational consulting services for nonprofit organizations, primarily in the Chicago area, through project-based and retainer-based engagements
Price-
Revenue$720K
EBITDA$395K

Retail Installation Services

Provides nationwide retail installation and project management for b2b fixture, millwork, signage and graphics manufacturers, including multi-trade electrical and flooring services on a project basis
Price-
Revenue$9.3M
EBITDA$1M

Asphalt Repair & Site Services

Provides commercial exterior and site services including asphalt parking lot work, street patches, concrete sidewalk repairs, power washing, and snow removal, with repeat project-based work for plumbing contractors restoring street surfaces after excavations
Price-
Revenue$800K
SDE$300K

Plastering Business

Provides plastering contracting services including acoustical plaster, cement plaster, cultured stone, and specialty finishes for major brands, construction and architectural firms, and public institutions on a project contract basis
Price$10.5M
Revenue$17M
EBITDA$1.8M

CNC Machine Business

Sells, services, and distributes CNC milling machines and parts across North America, holding exclusive U.S. distribution rights for a European high-precision machine line and a value-oriented line, primarily serving small to mid-sized machine shops and manufacturers including defense and aerospace customers
Price$300K
Revenue$482.8K
SDE$81.1K

Technical Content Creation Agency

Develops technical content engines for developer tools and platforms, providing strategy, production, and distribution services to help tech companies engage developer audiences through recurring subscription and retainer models
Price$800K
Revenue$1.2M
SDE$259.6K

Mail Sorting / Handling Service

Specializes in presorting First Class letters, flats, and packages to help businesses save on postage costs in Illinois.
Price-
Revenue$2.6M
EBITDA$276.4K
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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.