Businesses for Sale in Chicago, IL

Browse 260 businesses currently for sale in the Chicago, IL metro area with an average asking price of $1.4M. Find acquisition opportunities across every industry in the metro.

Active Listings
260
Median Asking Price
$692K
Median SDE
$192K
Median Multiple
3.5x SDE
Avg Asking Price
$1.4M
Average SDE
$307K
Listed in Last 30 Days
68
Added This Week
9

Median figures are computed over the 182 listings currently browsable on this page. Averages and counts cover all 260 active listings tracked in the last 90 days.

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Businesses for Sale in Chicago, IL

Showing 1–24 of 183

2w ago

Healthcare Practice for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$550KHealthcare & Wellness
Cash Flow:$200K
Multiple:2.8x
Why Buy

This home-based practice provides individualized behavioral therapy and related support services through a multi-clinician team. An existing client base, additional family inquiries, and an established clinical platform provide a foundation for continued growth.

Recurring RevenueGrowth TrajectoryRegulatory Risk
2w ago

Insurance Brokerage for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.0MProfessional Services
Cash Flow:$200K
Multiple:5.0x
Why Buy

The brokerage provides employee benefits and insurance services to business clients through long-term advisory relationships. Renewal commissions and client retention form the core of its recurring-revenue model.

Recurring RevenueSticky CustomersRegulatory Risk
2w ago

Pet Care Services for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$135KPersonal Services
Cash Flow:$93K
Multiple:1.5x
Why Buy

The business offers several pet care services, including walking, sitting, transportation, and waste removal. A loyal client base and multiple service lines create opportunities for repeat business and diversified revenue.

Recurring RevenueGrowth Trajectory
2w ago

Vending Machine Business for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$240KRetail & E-commerce
Cash Flow:$201K
Multiple:1.2x
Why Buy

This automated retail operation uses vending units to sell prepared foods, snacks, and drinks. The existing equipment and inventory provide a base from which a buyer can operate and potentially expand through additional locations.

2w ago

High-volume Profitable Cookie Shop for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$249KFood & Beverage
Why Buy

This dessert retail business is described as a high-volume operation with strong sales and reported cash flow. Its established franchise model may appeal to a buyer seeking an operating food retail business in the Chicago metropolitan region.

2w ago

Home Care Agency for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$470KHealthcare & Wellness
Cash Flow:$394K
Multiple:1.2x
Why Buy

The business provides personal care, companionship, and household assistance, complemented by specialized support programs. Its lean operating model and broad service offering position it to serve families across multiple care needs.

Growth TrajectoryRegulatory Risk
2w ago

Hvac Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$450KHome Services
Cash Flow:$123K
Multiple:3.7x
Why Buy

The company serves residential and commercial customers with HVAC installation and problem-solving services. A strong reputation and referral relationships generate ongoing demand without reliance on paid advertising.

Sticky CustomersKey Person Risk
2w ago

Electrical Contractor for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$260KHome Services
Cash Flow:$190K
Multiple:1.4x
Why Buy

This residential electrical service business handles repairs, evaluations, maintenance, and upgrades to household systems. Its range of services addresses ongoing safety and reliability needs, offering a buyer a service model with potential for repeat customer relationships.

3w ago

Restaurant And Catering for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$675KFood & Beverage
Cash Flow:$180K
Multiple:3.8x
Why Buy

This food-service business brings together a restaurant, mobile food service, and catering to serve a broad range of dining and event needs. Its multiple sales channels and reported cash flow may offer a buyer several avenues for maintaining and developing the business.

Recurring RevenueSticky CustomersGrowth Trajectory
4w ago

Recurring Scalable Lawn Care Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$255KHome Services
Cash Flow:$209K
Multiple:1.2x
Why Buy

This seasonal lawn care business is built around scheduled treatments that encourage repeat customer engagement and predictable service demand. Centralized scheduling and payment support may help keep administration manageable while leaving room to expand service offerings in Illinois.

Recurring Revenue
Sep 13

Fast Casual Restaurant for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$300KFood & Beverage
Why Buy

The restaurant combines a drive-through with indoor dining and established kitchen preparation processes. Its long operating history and existing service infrastructure may appeal to a buyer seeking an established food-service business in the Chicago metropolitan area.

Sticky CustomersRetirement Sale
Sep 11

Cabinet Manufacturer for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.5MManufacturing & Production
Why Buy

The business sells, assembles, and distributes cabinetry through a showroom serving consumer and commercial customers. Reported sales, cash flow, and seller financing availability may offer a buyer an established platform with multiple customer channels.

Recurring Revenue
Sep 11

Sign Manufacturing Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$175KManufacturing & Production
Why Buy

The business manufactures signs and has an established presence in its market. Reported cash flow and a long-running owner-operated business model may appeal to a buyer seeking a small manufacturing operation.

Sep 11

Truck Parts Distributor for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.5MWholesale & Distribution
Why Buy

The business supplies truck and trailer parts to transportation and emergency-service customers. Its established customer relationships and reported cash flow may appeal to a buyer seeking a specialized distribution operation.

Sticky Customers
Sep 11

Food Wholesale Distributor for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$500KWholesale & Distribution
Why Buy

The business supplies food products to a longstanding customer base and reports substantial annual sales and cash flow. Its established client relationships and wholesale model may appeal to a buyer seeking a business with repeat commercial demand.

Sticky Customers
Sep 11

Roofing Contractor for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$4.5MConstruction & Trades
Why Buy

The contractor serves residential and commercial customers with roofing and related exterior restoration work, including insurance-driven projects. Reported revenue, project-level margins, and near-term business visibility may appeal to a buyer seeking a growth-oriented construction platform.

Growth Trajectory
Sep 11

Floor Coating Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$150KHome Services
Why Buy

The business installs floor coatings for residential, commercial, and industrial customers and operates from a home-based, relocatable model. Reported cash flow and demand across several customer segments may appeal to a buyer seeking a flexible service business.

Key Person Risk
Sep 11

Auto Repair Shop for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$319KAutomotive Services
Why Buy

The business provides automotive services through a franchise operation with an established reputation and customer base. Reported cash flow and a high-visibility setting may appeal to a buyer seeking an operating auto-service business.

Sticky Customers
Sep 11

Freight And Logistics Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$4.0MTransportation & Logistics
Why Buy

The business combines asset-based freight transportation with cross-dock and warehouse operations. Reported revenue and cash flow across complementary logistics services may appeal to a buyer seeking a scaled transportation platform.

High CapEx
Sep 11

Exterior Maintenance Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$125KHome Services
Why Buy

The business provides deck and patio cleaning, staining, and sealing services, using subcontractors to support delivery. Its established customer demand and reported cash flow may appeal to a buyer seeking a service operation with a subcontractor-based model.

High Seasonality
Sep 11

Accounting Firm for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.2MProfessional Services
Why Buy

The practice provides tax, accounting, and payroll services, supported by staff and a diversified client offering. Its reported revenue and cash flow may appeal to a buyer seeking an established professional-services operation.

Recurring RevenueSticky Customers
Sep 11

Trucking And Logistics Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$3.8MTransportation & Logistics
Why Buy

The business provides trucking and logistics services to a diverse base of corporate customers across the Midwest. Its established client relationships and reported cash flow may appeal to a buyer seeking a regional transportation operation.

Recurring RevenueSticky Customers
Sep 11

Home Improvement Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$290KHome Services
Cash Flow:$139K
Multiple:2.1x
Why Buy

This home improvement business designs customized storage solutions and uses outside crews for installation. A home-based model and direct sourcing help limit overhead, while visual design tools support the customer consultation process.

Growth Trajectory
Sep 10

Property Restoration Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$140KHome Services
Cash Flow:$800K
Multiple:0.2x
Why Buy

This needs-based restoration company serves residential and commercial customers with fire, water, storm, mold, and remediation services. Its scalable model, strong margins, and recession-resistant demand create appeal for an owner focused on financial oversight and market development in the Chicago metropolitan area.

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Frequently Asked Questions

How many businesses are for sale in Chicago, IL?
Searcher OS currently tracks 260 businesses for sale in the Chicago, IL metro area, aggregated daily from broker websites and the major marketplaces. 9 of them were listed in the last 7 days. Locations are shown at the metro level — exact cities and broker contacts unlock with a free account.
How much does a business cost in Chicago, IL?
The median asking price of current listings is $692,000, and average seller's discretionary earnings run around $307,000. Most small businesses trade at a multiple of cash flow, so compare the asking price against earnings rather than revenue.
What multiple of earnings do businesses in the Chicago, IL metro area list for?
Across the 182 businesses currently browsable in the Chicago, IL metro area, the median asking price is $692K and the median seller's discretionary earnings (SDE) is $192K. The median asking price works out to 3.5x SDE. Multiples vary with size, growth, and owner dependence, so treat this as a benchmark rather than a rule.
Can I buy a business in Chicago, IL with an SBA loan?
Usually, yes. Most businesses in this size range qualify for SBA 7(a) acquisition financing, which typically covers up to 90% of the purchase price on a 10-year term, leaving a 10–15% down payment. Lenders look for steady cash flow that covers the loan payments with room to spare (debt service coverage), so listings with documented earnings are the easiest to finance.
How do I find businesses for sale in Chicago, IL before other buyers?
Most listings appear on individual broker websites days or weeks before they reach the national marketplaces. Searcher OS scrapes those broker sites daily and matches new Chicago, IL listings against your acquisition criteria, so you can be the first call instead of one of fifty.

Buying a Business in Chicago, IL

The Chicago, IL metro area supports a steady flow of small-business acquisitions across service, retail, and industrial sectors. Buying close to home has real advantages: you can meet sellers face to face, judge locations and crews yourself, and keep the local customer relationships that make these businesses durable after a transition.

Listings here are shown at the metro level to protect seller confidentiality — the exact city, full description, and broker contact unlock with a free account. Most businesses in this size range qualify for SBA 7(a) financing with 10–15% down, so compare each deal's cash flow against its projected debt service, not just the asking price. Start with these guides:

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