Real Estate Investment Properties for Sale in Chicago, IL

Looking for investment property in Chicago, IL with high ROI ?

Explore a variety of short-term homes & houses in Chicago, IL. Invest wisely with VRBO & Chicago, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Chicago, IL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
11616 S Harvard Avenue Chicago, IL	3 beds \| 2 baths \| 1,200 sq.ft.	$219,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 7.39% Airbnb Rental Income: $1360 Traditional Rental Income: $1940 Airbnb ROI: 2.61% Traditional ROI: 7.39%
7801 S Ada Street Chicago, IL Welcome to this stunning, fully remodeled solid-brick single-family home in Auburn Gresham...	3 beds \| 3 baths \| 1,200 sq.ft.	$240,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 8.19% Airbnb Rental Income: $659 Traditional Rental Income: $2306 Airbnb ROI: -0.39% Traditional ROI: 8.19%
5918 S Albany Avenue Chicago, IL GREAT OPPORTUNITY TO OWN IN THIS FAST APPRECIATING AREA !!! REAR OF THE LOT !!BRICK SINGLE...	2 beds \| 2 baths \| 832 sq.ft.	$175,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 9.26% Airbnb Rental Income: $974 Traditional Rental Income: $2024 Airbnb ROI: 0.85% Traditional ROI: 9.26%
1722 N Keeler Avenue Chicago, IL Hot Hermosa location! Updated single family home on a great block. House went through exte...	3 beds \| 1 baths \| 842 sq.ft.	$259,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 4.25% Airbnb Rental Income: $1188 Traditional Rental Income: $1632 Airbnb ROI: 0.86% Traditional ROI: 4.25%
5229 W Carmen Avenue Chicago, IL Charming, updated farmhouse on an extra-wide lot in Jefferson Park! This inviting home ble...	3 beds \| 2 baths \| 1,394 sq.ft.	$485,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 1.99% Airbnb Rental Income: $844 Traditional Rental Income: $2117 Airbnb ROI: -1.54% Traditional ROI: 1.99%
130 S Canal Street unit: 9F Chicago, IL Prime West Loop Duplex Offers Strong Value & Location! This 2-bedroom, 2.5-bath duplex con...	2 beds \| 3 baths \| 1,800 sq.ft.	$594,900	Airbnb cash on cash: -1.8% Traditional cash on cash: 2.45% Airbnb Rental Income: $1081 Traditional Rental Income: $3072 Airbnb ROI: -1.8% Traditional ROI: 2.45%
1432 W Chase Avenue Chicago, IL **Seller has accepted an offer in the evening on Fri, March 20. Paperwork still being sign...	4 beds \| 2 baths \| 2,046 sq.ft.	$600,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.19% Airbnb Rental Income: $1439 Traditional Rental Income: $2269 Airbnb ROI: -1.06% Traditional ROI: 1.19%
7216 S CENTRAL PARK Avenue Chicago, IL Well-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi...	3 beds \| 2 baths \| 1,080 sq.ft.	$290,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 6.32% Airbnb Rental Income: $575 Traditional Rental Income: $2371 Airbnb ROI: -1.29% Traditional ROI: 6.32%
4836 S Dorchester Avenue Chicago, IL Stunning 3-Flat Georgian Style Multi-Family Building in the Hyde Park/Kenwood Community, w...	6 beds \| 5 baths \| N/A	$950,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 0.59% Airbnb Rental Income: $2824 Traditional Rental Income: $2659 Airbnb ROI: 0.03% Traditional ROI: 0.59%
130 S CANAL Street unit: 724 Chicago, IL Experience the unmatched charm of this one-of-a-kind condo at Metropolitan Place in the he...	2 beds \| 2 baths \| 1,370 sq.ft.	$425,000	Airbnb cash on cash: -4.35% Traditional cash on cash: -0.41% Airbnb Rental Income: $1081 Traditional Rental Income: $2281 Airbnb ROI: -4.35% Traditional ROI: -0.41%
7018 S PAXTON Avenue unit: 3N Chicago, IL Luxury, fully renovated top floor 3-bedroom home. Finishes include beautiful cherry hardwo...	3 beds \| 2 baths \| 1,700 sq.ft.	$210,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 9.58% Airbnb Rental Income: $1094 Traditional Rental Income: $2452 Airbnb ROI: 0.89% Traditional ROI: 9.58%
3744 N Lockwood Avenue Chicago, IL FIRST FLOOR WITH 3 BEDROOMS AND 2 BATHS, INCLUDING MASTER SUITE. UPDATED KITCHEN INCLUDES ...	3 beds \| 3 baths \| N/A	$429,900	Airbnb cash on cash: -0.73% Traditional cash on cash: 5.42% Airbnb Rental Income: $1098 Traditional Rental Income: $3200 Airbnb ROI: -0.73% Traditional ROI: 5.42%
1211 S Prairie Avenue unit: 3401 Chicago, IL Experience elevated living in this stunning three bedroom, three and a half bathroom condo...	3 beds \| 4 baths \| 2,920 sq.ft.	$1,490,000	Airbnb cash on cash: -4.9% Traditional cash on cash: -2.63% Airbnb Rental Income: $598 Traditional Rental Income: $3455 Airbnb ROI: -4.9% Traditional ROI: -2.63%
1345 S Wabash Avenue unit: 408 Chicago, IL Welcome to this beautiful concrete loft in Chicago's vibrant South Loop neighborhood! This...	1 beds \| 1 baths \| 728 sq.ft.	$255,000	Airbnb cash on cash: -2.19% Traditional cash on cash: 3.99% Airbnb Rental Income: $974 Traditional Rental Income: $2111 Airbnb ROI: -2.19% Traditional ROI: 3.99%
175 E Delaware Place unit: 7204 Chicago, IL Welcome to your home in the sky, offering breathtaking North-facing views from the 72nd fl...	2 beds \| 2 baths \| 1,470 sq.ft.	$710,000	Airbnb cash on cash: -3.8% Traditional cash on cash: -1.72% Airbnb Rental Income: $1412 Traditional Rental Income: $2363 Airbnb ROI: -3.8% Traditional ROI: -1.72%
401 E Ontario Street unit: 1410 Chicago, IL Welcome to elevated city living at 401 E Ontario St - a beautifully positioned 14th-floor ...	1 beds \| 1 baths \| 900 sq.ft.	$345,000	Airbnb cash on cash: -4.05% Traditional cash on cash: 0.62% Airbnb Rental Income: $835 Traditional Rental Income: $2022 Airbnb ROI: -4.05% Traditional ROI: 0.62%
401 E ONTARIO Street unit: 707 Chicago, IL	1 beds \| 1 baths \| 800 sq.ft.	$299,999	Airbnb cash on cash: -3.75% Traditional cash on cash: 2.74% Airbnb Rental Income: $835 Traditional Rental Income: $2339 Airbnb ROI: -3.75% Traditional ROI: 2.74%
3301 N Ozanam Avenue Chicago, IL Excellent investment opportunity in a desirable Northwest Chicago neighborhood. This fully...	5 beds \| 3 baths \| N/A	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $2870 Airbnb ROI: N/A Traditional ROI: 3.14%
4248 S Drexel Boulevard unit: 3S Chicago, IL Live your best life overlooking the tree-lined boulevard in this sun drenched 3 bedroom, 2...	3 beds \| 2 baths \| 1,700 sq.ft.	$365,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 6.5% Airbnb Rental Income: $974 Traditional Rental Income: $3008 Airbnb ROI: -0.46% Traditional ROI: 6.5%
6033 N Sheridan Road unit: 8E Chicago, IL Welcome to this stunning, beautifully remodeled condo offering the perfect mix of modern e...	2 beds \| 2 baths \| 1,533 sq.ft.	$389,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 5.62% Airbnb Rental Income: $1402 Traditional Rental Income: $2913 Airbnb ROI: 0.32% Traditional ROI: 5.62%

Real Estate investment in Chicago, IL

There are 5,618 properties for sale in the city of Chicago . The median list price in Chicago is $389,000 and the average price per square foot is $229. In March 2026, the average monthly cash on cash return in Chicago is 2.00%. The average monthly rental income in Chicago is $2,240.

Chicago, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 5,618 investment properties available for sale in Chicago.

In 2026, the best neighborhood to buy investment property is Hanson Park.

The ROI for Long-Term is higher than the Short-Term in Chicago with average rental income of $2,240.

Your search for investment property begins and ends here

Investment Property for Sale in Chicago, IL

11616 S Harvard Avenue

Chicago, IL

3 beds | 2 baths | 1,200 sq.ft.

$219,900

Airbnb cash on cash: 2.61%

Traditional cash on cash: 7.39%

Airbnb Rental Income: $1360

Traditional Rental Income: $1940

Airbnb ROI: 2.61%

Traditional ROI: 7.39%

7801 S Ada Street

Chicago, IL

3 beds | 3 baths | 1,200 sq.ft.

$240,000

Airbnb cash on cash: -0.39%

Traditional cash on cash: 8.19%

Airbnb Rental Income: $659

Traditional Rental Income: $2306

Airbnb ROI: -0.39%

Traditional ROI: 8.19%

5918 S Albany Avenue

Chicago, IL

2 beds | 2 baths | 832 sq.ft.

$175,000

Airbnb cash on cash: 0.85%

Traditional cash on cash: 9.26%

Airbnb Rental Income: $974

Traditional Rental Income: $2024

Airbnb ROI: 0.85%

Traditional ROI: 9.26%

1722 N Keeler Avenue

Chicago, IL

3 beds | 1 baths | 842 sq.ft.

$259,900

Airbnb cash on cash: 0.86%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $1188

Traditional Rental Income: $1632

Airbnb ROI: 0.86%

Traditional ROI: 4.25%

5229 W Carmen Avenue

Chicago, IL

3 beds | 2 baths | 1,394 sq.ft.

$485,000

Airbnb cash on cash: -1.54%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $844

Traditional Rental Income: $2117

Airbnb ROI: -1.54%

Traditional ROI: 1.99%

130 S Canal Street unit: 9F

Chicago, IL

2 beds | 3 baths | 1,800 sq.ft.

$594,900

Airbnb cash on cash: -1.8%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $1081

Traditional Rental Income: $3072

Airbnb ROI: -1.8%

Traditional ROI: 2.45%

1432 W Chase Avenue

Chicago, IL

4 beds | 2 baths | 2,046 sq.ft.

$600,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $1439

Traditional Rental Income: $2269

Airbnb ROI: -1.06%

Traditional ROI: 1.19%

7216 S CENTRAL PARK Avenue

Chicago, IL

3 beds | 2 baths | 1,080 sq.ft.

$290,000

Airbnb cash on cash: -1.29%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $575

Traditional Rental Income: $2371

Airbnb ROI: -1.29%