Businesses for sale in Chicago, IL
Want to buy a business in Chicago? This page rounds up Chicago listings from public listing sites and brokers, and searching them is free. Neighborhood names come up constantly here: Logan Square bakeries, Lincoln Park restaurants and med spas, Old Town gyms, Lincoln Square nail salons, and staffing franchises in the West Loop. You'll also see laundromats, window cleaning routes, medical and therapy practices, and the occasional car dealership. Many asking prices here land well under a million dollars, a realistic range for a first-time buyer. When a seller shares enough numbers, we add a cash-on-cash estimate on our model, a quick way to compare a pizzeria against a salon before you call anyone. Searching the Chicago suburbs instead? We have a separate Naperville page for the west suburbs.
Estimates only — not financial, tax, or legal advice.
2,192 in Chicago · 3,483 including nearby Cook County suburbs
- 2,192listings for sale in Chicago
- 138clear 20% cash-on-cash on our model, incl. nearby towns
- 143clear 1.5x DSCR on our model, incl. nearby towns
Counts include operating businesses and commercial property (2,890 property listings, tagged). Cash-on-cash and DSCR counts cover operating businesses only. Estimate only — not financial or investment advice. Modeled at 30% down, 7.5% interest and a 10-year loan. Listings with implausible figures, placeholder prices or cannabis businesses aren't counted. How we estimate
Businesses for sale in and near Chicago
Showing 2,089–2,112 of 3,483. Listings in Chicago come first, then nearby towns; within each, businesses before commercial property, the most recently seen first.
Listings not seen recently may already be sold or changed, so check the broker's page.
- CrexiCommercial property3541 W Diversey AvenueChicago, IL · Multifamily$470,000Last seen Sep 9, 2026Multifamily
- Ask
- $470k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property57 E Cedar StreetChicago, IL · Multifamily$1,699,990Last seen Sep 9, 2026Multifamily
- Ask
- $1.7M
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property4150 W CARROLL AvenueChicago, IL · Multifamily$130,000Last seen Sep 9, 2026Multifamily
- Ask
- $130k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property3509 W Lexington StreetChicago, IL · Multifamily$300,000Last seen Sep 9, 2026Multifamily
- Ask
- $300k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property5338 S Wood StreetChicago, IL · Multifamily$149,900Last seen Sep 9, 2026Multifamily
- Ask
- $150k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property1019 W 18th StreetChicago, IL · Multifamily$859,999Last seen Sep 9, 2026Multifamily
- Ask
- $860k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property8462 S Commercial AvenueChicago, IL · Multifamily$249,000Last seen Sep 9, 2026Multifamily
- Ask
- $249k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property2037 N Tripp AvenueChicago, IL · Multifamily$449,900Last seen Sep 9, 2026Multifamily
- Ask
- $450k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property1229 E 71st StreetChicago, IL · Multifamily$330,000Last seen Sep 9, 2026Multifamily
- Ask
- $330k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property3709 N Bosworth AvenueChicago, IL · Multifamily$1,500,000Last seen Sep 9, 2026Multifamily
- Ask
- $1.5M
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property5364 N Latrobe AvenueChicago, IL · Multifamily$574,900Last seen Sep 9, 2026Multifamily
- Ask
- $575k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property7348 S Vernon AvenueChicago, IL · Multifamily$449,900Last seen Sep 9, 2026Multifamily
- Ask
- $450k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property2749 S Trumbull AvenueChicago, IL · Multifamily$375,000Last seen Sep 9, 2026Multifamily
- Ask
- $375k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property5455 S Kenwood AvenueChicago, IL · Multifamily$509,900Last seen Sep 9, 2026Multifamily
- Ask
- $510k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property5315 W Crystal StreetChicago, IL · Multifamily$274,900Last seen Sep 9, 2026Multifamily
- Ask
- $275k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property4836 S Dorchester AvenueChicago, IL · Multifamily$925,000Last seen Sep 9, 2026Multifamily
- Ask
- $925k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property3859 N Whipple StreetChicago, IL · Multifamily$900,000Last seen Sep 9, 2026Multifamily
- Ask
- $900k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property1002 N AVERS AvenueChicago, IL · Multifamily$449,900Last seen Sep 9, 2026Multifamily
- Ask
- $450k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property2250 S Sacramento AvenueChicago, IL · Multifamily$375,000Last seen Sep 9, 2026Multifamily
- Ask
- $375k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property6219 N Claremont AvenueChicago, IL · Multifamily$774,500Last seen Sep 9, 2026Multifamily
- Ask
- $775k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property2324 N Central Park AvenueChicago, IL · Multifamily$819,000Last seen Sep 9, 2026Multifamily
- Ask
- $819k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property4134 W 25th PlaceChicago, IL · Multifamily$325,000Last seen Sep 9, 2026Multifamily
- Ask
- $325k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property9133 S Essex AvenueChicago, IL · Multifamily$475,000Last seen Sep 9, 2026Multifamily
- Ask
- $475k
- Cash flow
- Not disclosed
- CoC · our model
- —
- CrexiCommercial property8125 S EVANS AvenueChicago, IL · Multifamily$315,000Last seen Sep 9, 2026Multifamily
- Ask
- $315k
- Cash flow
- Not disclosed
- CoC · our model
- —
Keep deals in one Desk
Save listings, run buy-box (CoC + DSCR), track NDAs, and sync Gmail. Desk is $20/month, no success fees.
- Unlimited pipeline & buckets
- To-do + NDA helpers
- Gmail sync & draft
- CoC + DSCR buy-box tools
- No success fees
Free to browse. A free account saves listings; Desk adds the deal tools.
Renews automatically at $20/month until you cancel. Cancel anytime online in Settings > Billing.