rejigg

Businesses for Sale in Chicago

Find businesses for sale in the Chicago metro area. Rejigg has 21+ active listings within 60 miles, spanning Illinois, Indiana and Wisconsin. The Windy City means serious business. World-class logistics through O'Hare, commodities trading at the CBOT, manufacturing heritage, and a thriving food scene make Chicago the business capital of the Midwest. Deep dish opportunities await. Each of these off-market businesses have been individually sourced and vetted by our team, and Rejigg makes it easy to connect directly with the owner. Create your account and get started today!

“I liked how easy it was to get connected with prospective sellers. We could easily find a time that worked and schedule a call through the platform.”

Rejigg buyer

21+

Active Listings

60mi

Search Radius

3

States Covered

Free

To Browse

Businesses within the Chicago Metro Area

Showing 10 of 21 listings within 60 miles of Chicago

Roofing Business

Offers services for roofing, siding, and gutters with a client base of 95% residential and 5% commercial in HOA subdivisions.
Price:$1.8M
Revenue:$2M
SDE:$401.2K

Regional Trucking & Logistics Company

Operates a fleet of 500 trucks, providing transportation solutions across North American corridors with diversified revenue streams including contract carriage, spot market, and value-added services.
Price:$45M
Revenue:$135.8M
SDE:$10.3M

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

Digital Marketing Agency

Provides customizable digital marketing services such as SEO, website design, social media management, and online reputation management to small and midsize businesses across 30 states and three countries, with revenue from monthly contracts and a 90% two-year retention rate.
Price:$2M
Revenue:$494.2K
EBITDA:$285.1K

Commercial Printing and Mailing Business

Provides a comprehensive range of printing, bindery, specialty finishing, and in-house mailing solutions to commercial clients and organizations across the United States, operating from a large facility in the Chicago area equipped with advanced offset and digital printing technology.
Price:$3M
Revenue:$3.5M
EBITDA:$700K

Landscaping Company

Specializes in integrated landscape design, installation, hardscapes, water features, lighting, lawn maintenance, pest control, and snow removal for residential and commercial clients in Illinois.
Price:$600K
Revenue:$1.2M
EBITDA:$49.7K

Auto Shop

Provides a full range of maintenance and repair services for domestic and foreign vehicles, including diagnostics, engine repair, brake and suspension work, transmission service, and routine maintenance, with business from individual owners and car rental companies.
Price:$1.7M
Revenue:$950K
SDE:$550K

Tech-Enabled Mental Healthcare Marketplace

Connects patients from the Latino community with psychologists for mental health services, earning revenue through transactions and subscriptions.
Price:$3.3M
Revenue:$917.3K
EBITDA:-$103K

Retail Installation Services

Specializes in retail installation and project management services nationwide, including fixture, millwork, signage, and graphic installations as well as multi-trade services like electrical and flooring, with a B2B client base consisting of manufacturers of display fixtures, graphics, decor elements, and millwork.
Price:-
Revenue:$9.3M
EBITDA:$1M

Consulting Firm for Nonprofit Organizations

Partners with mission-driven nonprofit organizations to advance fundraising, organizational development, and communications priorities through strategic planning, assessment, and implementation of capital campaigns, major gift programs, board development, and general fundraising services, serving over 300 clients primarily in the Chicago area.
Price:-
Revenue:$916.4K
EBITDA:$369.8K
Explore the other 11 Chicago businesses with filters

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Chicago Business Market Overview

The Chicago metropolitan area offers diverse business acquisition opportunities across Illinois, Indiana and Wisconsin. With a strong local economy and established business community, buyers can find profitable companies ready for new ownership.

Key Industries in Chicago

The Chicago market features businesses across logistics, commodities, manufacturing, food & beverage, professional services sectors. Many businesses have established customer bases and proven revenue streams, making them attractive acquisition targets for both first-time buyers and experienced entrepreneurs.

Why Buy in Chicago?

Acquiring a business in the Chicago area provides immediate access to an established customer base, trained workforce, and proven business model. Skip the startup phase and step into a cash-flowing operation with existing vendor relationships and market positioning.

Frequently Asked Questions About 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.

Benefits of Buying an Existing Company

Acquiring a well-established company is a strategic move that allows a buyer to avoid many of the challenges associated with getting a business off the ground and instead focus on scaling an established company. Here are some of the benefits of buying an existing business:

  • Assuming a proven business model

  • Access to an existing customer base

  • Access to an immediate cash flow stream

  • Allows you to focus on optimization and expansion

See examples of successful acquisitions in our recent transactions, or explore our articles for acquisition guides and insights.

Benefits of buying an existing business
Simplifying Business Acquisition

At Rejigg, we are trying to build a platform that simplifies the process of finding and buying a high-quality business:

Learn more about Rejigg and how we connect buyers with sellers. Check out our pricing for details on how we work with buyers.

We source high-quality leads, and collect all the information that you need to get started. Rest assured, you'll be talking with a qualified and motivated seller.

Our platform enables direct communication between buyers and sellers to foster transparency and trust.

Our team provides support as needed throughout the acquisition process, without getting in the way. Most often this means providing referrals for legal resources, tax advice, quality of earnings reporting, or other third party services.

Need help evaluating a deal? Try our SBA Calculator to understand financing options, or use our Success Fee Calculator to see how our pricing works at different transaction sizes.

How Do I Get Started?

Finding your ideal business with Rejigg is easy and straightforward. Explore our off-market listings to find a business opportunity that matches your interests and budget. By signing up, you can unlock access to a wide variety of exclusive business listings. With our user-friendly search tools, you can narrow down your options based on your budget, business goals, and personal interests. Once you find a business that catches your attention, reach out to the seller to connect directly.

Sign Up and Review all of Our Listings

Our sign-up process is simple and quick. After you sign up, you will have immediate access to our list of businesses for sale. Quickly search and filter to find the opportunities that are right for you.

Complete Your Buyer Profile

Your buyer profile includes a brief biography, your target business description, and your planned sources of financing. We share this information with sellers when you request a conversation so that they have enough context and can feel confident that they're talking with a qualified buyer.

Get in Touch With Sellers

Once you shortlist a business, you can easily connect with the seller through our platform. You can message back and forth and schedule an introductory call directly through the platform. From there, you're off to the races.

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