Businesses for Sale in Chicago, IL

Browse 270 businesses currently for sale in the Chicago, IL metro area with an average asking price of $1.6M. Find acquisition opportunities across every industry in the metro.

Active Listings
270
Avg Asking Price
$1.6M
Average SDE
$302K
Added This Week
16

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Businesses for Sale in Chicago, IL

Showing 97120 of 130

Jun 10

Bridal Retail Store for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$3.3MRetail & E-commerce
Cash Flow:$469K
Multiple:7.0x
Why Buy

This Illinois bridal retailer operates from a large, well-appointed showroom in a high-income market, maintaining a 67% close rate on consultations and growing revenue more than 12% annually. Over 1,000 gowns in stock and a team of trained consultants provide a premium, personalized experience that drives strong word-of-mouth and repeat referrals within the wedding market. SBA pre-qualification and $100,000 of included inventory lower the effective acquisition cost for a qualified buyer.

Growth Trajectory
Jun 10

Montessori School for Sale in Chicago, IN

Chicago-Naperville-Elgin, IN
$725KEducation & Training
Cash Flow:$145K
Multiple:5.0x
Why Buy

This early childhood education center has operated for 50 years in the greater Chicago metro area, building deep community trust and a strong academic reputation serving children from infancy through kindergarten age. The purpose-built facility has been recently upgraded across HVAC, roofing, security, and outdoor spaces, reducing near-term capital expenditure needs for a new owner. A tenured staff and proven enrollment model provide a stable operational foundation in a structurally undersupplied childcare market.

Recurring RevenueSticky CustomersGrowth Trajectory
Jun 10

Truck And Auto Repair for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.7MAutomotive Services
Cash Flow:$110K
Multiple:15.8x
Why Buy

A well-established repair facility in the Chicago metro area serving a mix of commercial diesel truck and consumer vehicle repair with limited local competition in the commercial segment. The 80% diesel revenue concentration positions the business in a higher-ticket, less price-sensitive customer category where strong goodwill and technical reputation drive repeat business. Established community relationships and an existing customer base provide a durable revenue foundation for a new owner-operator.

Jun 10

Orthopedic Medical Practice for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.9MHealthcare & Wellness
Cash Flow:$579K
Multiple:3.3x
Why Buy

A multi-provider orthopedic practice in the Chicago suburbs with over three decades of operating history, a 9,000 square foot facility, and a referral-dominant patient acquisition model. The practice treats a broad range of musculoskeletal conditions and has maintained consistent profitability from a stable provider team and loyal patient base. Seller willingness to remain through transition reduces continuity risk for a new physician owner or practice management group.

Sticky Customers
Jun 10

Flagged Motel for Sale in Chicago, IN

Chicago-Naperville-Elgin, IN
$4.0MEntertainment & Recreation
Cash Flow:$250K
Multiple:16.0x
Why Buy

A 122-room flagged motel in the Chicago metro area generates $1.3M in room revenue with no PIP required, keeping upfront capital needs low for an acquiring buyer. The property currently operates under absentee management, suggesting meaningful upside for an engaged owner-operator who can optimize occupancy and operational efficiency. Asking price of $4M with $250K in SDE positions this as a hospitality acquisition for a buyer seeking a branded flag in a high-demand corridor.

Absentee Owner
Jun 10

Specialty Lingerie Retail Store for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$575KRetail & E-commerce
Cash Flow:$118K
Multiple:4.9x
Why Buy

This Chicago-area specialty undergarment retailer operates in a niche with minimal direct competition, serving a loyal clientele in a well-trafficked, upscale retail environment. The current owner runs the business near-absentee, suggesting strong systems and staff in place, and sees clear growth potential through digital marketing and automation that the next owner could unlock. With approximately $118K in annual cash flow on a $575K asking price, the business offers modest returns with meaningful upside from a more engaged operator.

Absentee OwnerSticky CustomersGrowth Trajectory
Jun 10

Cash-flowing Turnkey Flagged Hotel for Sale in Chicago, IN

Chicago-Naperville-Elgin, IN
$6.9MEntertainment & Recreation
Cash Flow:$300K
Multiple:23.0x
Why Buy

A 70-room flagged hotel in the Chicago metro area generates $1.8M in room revenue with no property improvement plan (PIP) required, limiting near-term capital outlay for a buyer. The property is currently absentee-operated, indicating strong systems are in place, while also suggesting an active owner-operator could extract significantly more value. At a $6.9M asking price with $300K in SDE, this is a hospitality acquisition suited for an experienced operator seeking a branded flag in a major metro market.

Absentee Owner
Jun 10

Auto Body Repair Shop for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$699KAutomotive Services
Cash Flow:$191K
Multiple:3.7x
Why Buy

This full-service auto body repair facility in the Chicago metro area has operated for two decades with all major certifications, a stellar online review profile, and the added value of an auto dealer license included with the sale. The dealer license enables the new owner to purchase vehicles at auction, recondition them, and resell at a profit — a meaningful secondary revenue stream beyond collision repair. The clean, well-organized facility and strong community reputation position this business as a rare turn-key opportunity in a major metropolitan market.

Sticky Customers
Jun 10

Landscape Design Build Company for Sale in Chicago, IN

Chicago-Naperville-Elgin, IN
$1.8MHome Services
Cash Flow:$383K
Multiple:4.6x
Why Buy

This Northwest Indiana landscaping and garden center has been designing and building custom outdoor spaces for nearly four decades, with crews trained to execute from architectural blueprints on both residential and commercial projects. A complementary on-site garden center selling bulk supplies and plants provides additional revenue diversification beyond design-build project work. With approximately $383K in annual seller earnings, the business offers a well-rounded platform for a buyer interested in the landscaping sector.

Sticky CustomersHigh Seasonality
Jun 10

Mexican Restaurant & Bar for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$550KFood & Beverage
Cash Flow:$132K
Multiple:4.2x
Why Buy

This elevated Mexican restaurant and bar in the Chicago metro generates consistent revenue from a loyal local following, benefiting from its proximity to multiple dense residential neighborhoods and a strong catering business serving corporate and event clients. Regular wait times reflect strong organic demand with no reliance on heavy marketing spend. The combination of dine-in, bar, and catering revenue streams diversifies cash flow for a new owner.

Manager in PlaceRecurring RevenueSticky CustomersGrowth Trajectory
Jun 10

Facial Bar Franchise Portfolio for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.5MPersonal Services
Cash Flow:$285K
Multiple:5.3x
Why Buy

This multi-location facial bar portfolio in the Chicago metro area includes six operating locations plus exclusive territorial rights to develop two additional sites, representing a rare opportunity to acquire a scaled footprint in the fast-growing express skincare segment. The concept delivers results-focused 30-minute facial treatments at accessible price points, appealing to a broad consumer base that values efficiency. With a proven membership model and brand infrastructure already in place, a buyer can focus on operational optimization and franchise expansion.

Recurring RevenueGrowth Trajectory
Jun 10

Full Service Restaurant for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$599KFood & Beverage
Cash Flow:$230K
Multiple:2.6x
Why Buy

This Chicago suburban restaurant operates on a fully absentee basis, with an experienced staff managing all front- and back-of-house operations and financials independently verified by an outside CPA. The business has built a loyal destination-dining reputation with significant customer repeat rates, and revenue has trended upward through the most recent period. Bank pre-approval and substantial transferable assets reduce a buyer's financing and startup risk.

Absentee OwnerGrowth TrajectoryRecurring Revenue
Jun 9

Wellness Subscription Platform for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$800KTechnology & Software
Cash Flow:$30K
Multiple:26.7x
Why Buy

A subscription-based digital wellness and personal development platform serves over 200 active paying customers through guided programs, habit tracking, and goal-setting tools, generating recurring revenue with a single operator managing day-to-day operations. The business is structured as an LLC and operates entirely online, eliminating geographic constraints for a new owner. At $800K asking price with $30K in SDE, the valuation reflects platform and subscriber acquisition upside rather than current earnings, making this a fit for a buyer focused on growth over near-term cash flow.

Recurring RevenueSticky CustomersRevenue Decline
Jun 9

Trucking & Freight Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$6.0MTransportation & Logistics
Cash Flow:$1.0M
Multiple:6.0x
Why Buy

This Illinois trucking and logistics company has operated for nearly two decades, generating over $5M in annual revenue and approximately $1M in annual SDE with a fully owned fleet of 17 tractors and 20 trailers transferred free and clear. The business benefits from long-standing customer relationships, experienced personnel, and a proven operating infrastructure that supports continued growth. At a $5.95M asking price with significant hard-asset value embedded, this is a compelling acquisition for a logistics operator or strategic buyer seeking an established transportation platform in the Chicago region.

Sticky CustomersGrowth TrajectoryHigh CapEx
Jun 5

Industrial Parts Distributor for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.4MWholesale & Distribution
Cash Flow:$447K
Multiple:3.2x
Why Buy

A Midwest-based distributor of OEM and MRO industrial parts and kits serves a multi-state wholesale customer base with a catalog exceeding 25,000 unique SKUs and approximately 10 million pieces in stock sourced from thousands of vendors. The business also provides custom kit assembly to customer specifications, adding a value-added service layer to the distribution model. With nearly $450,000 in adjusted SDE and a well-organized inventory infrastructure in the Chicago area, the operation offers a reliable platform for an owner-operator or strategic acquirer.

Jun 5

Family Amusement And Water for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$5.9MEntertainment & Recreation
Cash Flow:$795K
Multiple:7.4x
Why Buy

A multi-attraction family entertainment destination in the Chicago metro area with over 60 years of operating history serves more than 170,000 annual guests across amusement rides, water attractions, animal exhibits, an indoor ice arena, food and beverage, and retail. Diversified revenue streams from admissions, season passes, events, and ancillary spending provide resilience across seasonal cycles. A strong season pass base, multi-generational customer loyalty, and a long-term land lease structure offer a buyer a differentiated regional asset with a well-established demand foundation.

Sticky CustomersHigh SeasonalityHigh CapEx
Jun 4

Auto Repair Shop for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.5MAutomotive Services
Cash Flow:$200K
Multiple:7.5x
Why Buy

This specialty auto repair business in Chicago's North Suburbs has built a strong reputation serving premium vehicle owners, with a focus on high-end European brands that typically command above-market service rates and attract quality-conscious clientele. The asking price includes both the operating business and the underlying real estate on a prime corner location, providing the acquiring operator with significant hard asset value and elimination of lease risk. The combination of a specialty service niche, real estate inclusion, and established customer relationships makes this a differentiated opportunity in the automotive services sector.

Sticky Customers
Jun 4

Property Damage Restoration Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$299KHome Services
Cash Flow:$134K
Multiple:2.2x
Why Buy

This property damage restoration business in the Chicago metro area provides water damage, fire disaster restoration, mold remediation, and biohazard services to residential and commercial clients, backed by preferred vendor relationships with national and regional insurance carriers. The executively operated model requires the owner to focus on marketing and relationship management rather than field work, with operations structured to scale to any volume level. Insurance-backed recurring demand and high service margins relative to the asking price create a resilient and scalable cash flow profile.

Jun 3

Specialty Apparel Retail Store for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$575KRetail & E-commerce
Cash Flow:$118K
Multiple:4.9x
Why Buy

This specialty intimate apparel retailer operates in an affluent, high-traffic venue in the greater Chicago area with a loyal, repeat customer base and minimal direct competition in its niche category. The current owner runs the business on a near-absentee basis, indicating strong operational systems and staff independence that reduce transition risk. A buyer with customer relationship skills could meaningfully grow revenue through expanded digital outreach and automation, building on a stable existing foundation.

Absentee OwnerManager in Place
Jun 3

Precision Cnc Machining Shop for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$700KManufacturing & Production
Cash Flow:$139K
Multiple:5.0x
Why Buy

This precision manufacturing job shop in Northeastern Illinois has operated for over four decades, producing custom machined components for a wide range of industries including medical, automotive, packaging, and food production. Modern CNC technology and a flexible job-shop model allow the business to serve diverse customers across small-to-medium batch production requirements, reducing dependence on any single sector. An experienced team, strong client relationships, and a modernized facility provide a buyer with a well-maintained platform requiring minimal immediate capital investment.

Jun 3

Residential Landscaping Company for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$2.0MHome Services
Cash Flow:$538K
Multiple:3.7x
Why Buy

This Chicagoland landscaping company has operated for over five decades serving one of the Chicago metro area's most affluent suburban markets, with the majority of revenue derived from recurring maintenance contracts. The business generates approximately $537,000 in annual SDE on a roughly $2 million asking price, with predictable cash flow supported by long-term client relationships and strong word-of-mouth referrals. Meaningful upside exists through expansion of hardscape, outdoor living, lighting, and seasonal services beyond the current maintenance focus.

Recurring RevenueSticky CustomersGrowth TrajectoryHigh Seasonality
Jun 2

Audit & Assurance Practice for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.6MProfessional Services
Cash Flow:$225K
Multiple:6.9x
Why Buy

This Chicago-area audit practice generates over $1.2 million in annual revenue from a loyal client base concentrated in multifamily and nonprofit audit engagements — recurring, relationship-driven work that renews year over year. Experienced CPAs and remote staff are in place, and the practice operates on well-established audit software, enabling a smooth transition for an acquiring CPA or firm. The client base can either remain in its current location or be integrated into a buyer's existing office.

Recurring RevenueSticky CustomersRetirement SaleKey Person Risk
May 30

High-margin Established Cpa Practice for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$1.6MProfessional Services
Cash Flow:$655K
Multiple:2.4x
Why Buy

This well-positioned CPA firm in the Chicago metro area serves a book of business heavily weighted toward business owners and high-net-worth individuals, producing cash flow above 60% of gross revenue. Revenue is diversified across high-end tax work, accounting and bookkeeping, and payroll and consulting engagements. The seller's willingness to support a long-term transition reduces key-person risk and supports client retention through an ownership change.

Recurring RevenueSticky CustomersKey Person Risk
May 29

Cpa & Accounting Firm for Sale in Chicago, IL

Chicago-Naperville-Elgin, IL
$266KProfessional Services
Cash Flow:$76K
Multiple:3.5x
Why Buy

This accounting, tax preparation, and bookkeeping practice in the western suburbs of Chicago generates strong annual revenue relative to its asking price, reflecting a buyer-friendly acquisition multiple. Professional services firms with recurring client relationships and predictable seasonal demand provide stable earnings for incoming owners. The business is well-positioned for an accounting professional seeking an established book of business or a firm looking to expand in the Chicago metro market.

Recurring RevenueSticky Customers

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Frequently Asked Questions

How many businesses are for sale in Chicago, IL?
Searcher OS currently tracks 270 businesses for sale in the Chicago, IL metro area, aggregated daily from broker websites and the major marketplaces. 16 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 $718,000, and average seller's discretionary earnings run around $302,000. Most small businesses trade at a multiple of cash flow, so compare the asking price against earnings rather than revenue.
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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