Businesses for Sale in Chicago, IL

Browse 258 businesses currently for sale in the Chicago, IL metro area with an average asking price of $1.7M. Find acquisition opportunities across every industry in the metro.

Active Listings
258
Median Asking Price
$700K
Median SDE
$203K
Median Multiple
3.6x SDE
Avg Asking Price
$1.7M
Average SDE
$348K
Listed in Last 30 Days
101
Added This Week
10

Median figures are computed over the 206 listings currently browsable on this page. Averages and counts cover all 258 active listings tracked in the last 90 days.

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Businesses for Sale in Chicago, IL

Showing 25–48 of 209

Sep 1

Established Profitable Bar And Grill for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.2MFood & Beverage
Cash Flow:$180K
Multiple:6.7x
Why Buy

This established high-volume bar and grill includes the underlying land and building in the greater Chicago region. A full kitchen, loyal customer base, and experienced staff provide an operating foundation with real estate ownership and transition support included.

Jul 19

Fence Installation Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$450KHome Services
Cash Flow:$124K
Multiple:3.6x
Why Buy

This established fencing company provides installation, repair, and replacement services to residential and commercial customers in the Chicago region. Its reputation, diversified service offering, and positive cash flow create a solid base for an owner-operator or strategic buyer.

Sep 1

Foundation Repair Contractor for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$943KConstruction & Trades
Cash Flow:$320K
Multiple:2.9x
Why Buy

This Illinois-based contractor provides specialized foundation stabilization, concrete raising, and structural repair services for residential, commercial, industrial, and municipal customers. Complementary seasonal snow-removal work supports year-round utilization and broadens the revenue base.

High Seasonality
Sep 1

Disaster Restoration Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$2.1MHome Services
Cash Flow:$392K
Multiple:5.4x
Why Buy

This Illinois restoration company serves residential and commercial customers with water, fire, mold, environmental, contents, cleaning, and reconstruction-related services. Experienced production leadership, commercial equipment, vehicles, subcontractor relationships, and documented processes support efficient project execution and continued growth.

Manager in PlaceGrowth Trajectory
Sep 1

Profitable Turnkey Pizza Restaurant for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$630KFood & Beverage
Cash Flow:$243K
Multiple:2.6x
Why Buy

This established pizza restaurant combines dine-in, bar, and sports-viewing revenue with consistent sales and strong cash flow in the Chicago metropolitan area. Absentee-friendly operations, experienced management, reliable staff, modern equipment, and an established franchise-supported model offer a buyer a ready-to-run platform.

Absentee OwnerManager in PlaceSticky Customers
Sep 1

Medical Practice for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$2.0MHealthcare & Wellness
Cash Flow:$727K
Multiple:2.8x
Why Buy

This established medical practice combines primary care, pain management, rehabilitation, and acupuncture with recurring patient demand and in-house billing. It offers a turnkey platform for a physician or investor, with room to expand services and operating capacity in Illinois.

Sticky CustomersRecurring RevenueRetirement Sale
Aug 31

Senior Home Care Service for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$164KHealthcare & Wellness
Cash Flow:$126K
Multiple:1.3x
Why Buy

This non-medical home-support operation provides maintenance, light repairs, cleaning assistance, and outdoor upkeep for aging households and other residents seeking help at home. Recurring service plans, standardized offerings, and efficient scheduling support predictable demand and provide a durable platform aligned with the aging-in-place trend in Illinois.

Regulatory Risk
Aug 27

Turnkey Low-overhead Flooring Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$256KConstruction & Trades
Cash Flow:$143K
Multiple:1.8x
Why Buy

This shop-at-home flooring company sells and coordinates installation of residential floor coverings through a convenient in-home consultation model in the Chicago region. Low overhead, personalized service, and strong cash flow position it as an appealing alternative to traditional showroom-based retail.

Aug 26

Gas Station Convenience Store for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$5.9MRetail & E-commerce
Cash Flow:$481K
Multiple:12.3x
Why Buy

This established gas station and convenience store combines substantial fuel volume with growing inside sales and newer infrastructure. Included real estate and demonstrated operating growth provide a diversified platform in the Chicago-Naperville-Elgin metro area.

Growth Trajectory
Aug 24

Medical Laboratory for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$700KHealthcare & Wellness
Cash Flow:$175K
Multiple:4.0x
Why Buy

This high-complexity toxicology laboratory offers specialized healthcare testing services within a regulated operating environment. Existing capabilities and reported profitability provide a buyer with a platform for serving clinical and institutional demand in Illinois.

Regulatory RiskHigh CapEx
Aug 24

Established Inventory-rich Gift Shop for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$245KRetail & E-commerce
Cash Flow:$50K
Multiple:4.9x
Why Buy

This established retail business offers a broad assortment of specialty gifts and hard-to-find merchandise, supported by substantial included inventory and strong traffic exposure in the Chicago metropolitan area. Retirement-driven ownership creates an opportunity for a buyer to acquire an operating store with existing customer appeal and room to optimize merchandising and sales.

Retirement Sale
Aug 24

Award-winning Profitable Restaurant for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$120KFood & Beverage
Cash Flow:$78K
Multiple:1.5x
Why Buy

This family-operated restaurant serves lunch and dinner with a menu centered on popular casual dining items. Its established reputation and attractive cash flow provide an opportunity for an owner-operator or experienced investor in the Chicago metropolitan area.

Aug 24

Commercial Cleaning Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$60KHome Services
Cash Flow:$30K
Multiple:2.0x
Why Buy

This cleaning service is built around a recurring client base and established customer relationships in the Chicago metropolitan area. The compact operating model may appeal to a buyer seeking a service business with existing accounts and opportunities to expand coverage.

Key Person Risk
Aug 24

Promotional Products Business for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$525KManufacturing & Production
Cash Flow:$164K
Multiple:3.2x
Why Buy

This home-based B2B operation serves repeat customers with embroidery, screen-printing, and promotional products, including larger and expedited orders shipped regionally and nationally. A buyer receives documented operating procedures, training materials, and the flexibility to relocate the operation within Illinois.

Sticky CustomersKey Person Risk
Aug 24

Recurring Scalable Senior Care Agency for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$279KHealthcare & Wellness
Cash Flow:$263K
Multiple:1.1x
Why Buy

This non-medical senior care organization provides daily living assistance, medication support, companionship, and housekeeping through structured transportation and service coordination. Monthly contracts, referral relationships, centralized administrative support, and strong reported cash flow create an attractive growth platform in Illinois.

Sticky Customers
Aug 24

Purpose-driven Growing Driving School for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$250KEducation & Training
Cash Flow:$118K
Multiple:2.1x
Why Buy

This driver education business delivers a parent-inclusive curriculum focused on accident prevention, confidence, and practical readiness rather than basic testing alone. A differentiated educational approach and strong instructor engagement create appeal for a buyer seeking a mission-oriented training business in Illinois.

Growth Trajectory
Aug 23

Growing Profitable Accounting Practice for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$820KProfessional Services
Cash Flow:$250K
Multiple:3.3x
Why Buy

This tax and accounting practice has grown through referrals and combines individual and business services with experienced staff support. Strong fee levels, recurring client demand, and an established operating platform offer expansion potential in the Chicago metropolitan area.

Recurring RevenueSticky CustomersGrowth TrajectoryHigh Seasonality
Aug 17

Tax Preparation Practice for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$226KProfessional Services
Cash Flow:$95K
Multiple:2.4x
Why Buy

This established tax practice serves a loyal recurring client base and reports strong average fees for individual returns. The retirement transition may create an opportunity for a buyer to acquire an established professional services platform in the Chicago region.

Recurring RevenueSticky CustomersRetirement SaleKey Person Risk
Aug 17

Accounting Practice for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$550KProfessional Services
Cash Flow:$204K
Multiple:2.7x
Why Buy

This established tax and accounting practice generates substantial recurring professional-services revenue and offers growth potential with flexible financing terms. Its existing client relationships and reported cash flow may appeal to a buyer seeking a platform in the Chicago region.

Recurring RevenueSticky Customers
Aug 17

Dryer Vent Cleaning Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$290KHome Services
Cash Flow:$142K
Multiple:2.0x
Why Buy

This dryer vent cleaning business addresses recurring household needs tied to safety, energy efficiency, and appliance performance. Low equipment requirements and overhead support a straightforward operating model with strong margins and appeal for a first-time or related-trade buyer.

Aug 15

Apparel E Commerce Brand for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$306KRetail & E-commerce
Cash Flow:$134K
Multiple:2.3x
Why Buy

This e-commerce apparel brand sells specialty wool clothing through an online retail model. Its ethical sourcing position, broad digital reach, and reported cash flow offer opportunities for continued brand and customer development.

Aug 11

Modern Scalable Fitness Studio for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$550KHealthcare & Wellness
Cash Flow:$75K
Multiple:7.3x
Why Buy

This boutique fitness studio uses a premium membership model supported by operational systems, vendor relationships, and marketing infrastructure. Its recurring-revenue structure and flexible management design may appeal to owner-operators, semi-absentee investors, and multi-unit entrepreneurs.

Recurring RevenueGrowth Trajectory
Aug 10

Profitable Turnkey Accounting Practice for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$325KProfessional Services
Cash Flow:$162K
Multiple:2.0x
Why Buy

This established accounting practice generates recurring professional-services revenue and is positioned as a turnkey acquisition. Available financing and a retirement-oriented transition create an accessible opportunity for a buyer seeking an established client base in the greater Chicago region.

Retirement SaleKey Person RiskRegulatory Risk
Aug 10

Established Turnkey Staffing Agency for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$70KProfessional Services
Cash Flow:$50K
Multiple:1.4x
Why Buy

This staffing and recruiting agency offers an existing book of business, trained personnel, and furnished operations. Its turnkey structure and low acquisition cost provide a buyer with a practical platform to expand within the greater Chicago employment market.

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Frequently Asked Questions

How many businesses are for sale in Chicago, IL?
Searcher OS currently tracks 258 businesses for sale in the Chicago, IL metro area, aggregated daily from broker websites and the major marketplaces. 10 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 $700,000, and average seller's discretionary earnings run around $348,000. 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 206 businesses currently browsable in the Chicago, IL metro area, the median asking price is $700K and the median seller's discretionary earnings (SDE) is $203K. The median asking price works out to 3.6x 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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