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
13223 S Buffalo Ave Chicago, IL Nicely updated Bungalow with Basement in a Great Location in Hegewisch! Features a sun-fil...	3 beds \| 2 baths \| 1,100 sq.ft.	$199,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 7.5% Airbnb Rental Income: $898 Traditional Rental Income: $1876 Airbnb ROI: 0.53% Traditional ROI: 7.5%
13210 S Carondolet Ave Chicago, IL 13210 S Carondolet Ave, Chicago, IL 60633 \| Single Family Residential	2 beds \| 2 baths \| 1,700 sq.ft.	$239,900	Airbnb cash on cash: -2.21% Traditional cash on cash: 5.28% Airbnb Rental Income: $617 Traditional Rental Income: $2024 Airbnb ROI: -2.21% Traditional ROI: 5.28%
11616 S Harvard Ave Chicago, IL Be the first to move into this fully renovated home, on a DOUBLE lot, located on a quiet b...	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 St Chicago, IL Welcome to this stunning, fully remodeled solid-brick single-family home in Auburn Gresham...	4 beds \| 3 baths \| 1,200 sq.ft.	$240,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 8.19% Airbnb Rental Income: $708 Traditional Rental Income: $2306 Airbnb ROI: -0.21% Traditional ROI: 8.19%
4131 W Belmont Ave #402 Chicago, IL 4131 W Belmont Ave #402, Chicago, IL 60641 \| Condo/Coop	2 beds \| 2 baths \| 1,102 sq.ft.	$375,000	Airbnb cash on cash: -3.09% Traditional cash on cash: 1% Airbnb Rental Income: $1082 Traditional Rental Income: $2152 Airbnb ROI: -3.09% Traditional ROI: 1%
5130 S Menard Ave Chicago, IL 5130 S Menard Ave, Chicago, IL 60638 \| Single Family Residential	3 beds \| 1 baths \| 945 sq.ft.	$290,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 2.1% Airbnb Rental Income: $1115 Traditional Rental Income: $1551 Airbnb ROI: -0.87% Traditional ROI: 2.1%
5801 S Blackstone Ave Chicago, IL 5801 S Blackstone Ave, Chicago, IL 60637 \| Single Family Residential	5 beds \| 4 baths \| 3,919 sq.ft.	$1,975,000	Airbnb cash on cash: -2.13% Traditional cash on cash: -1.51% Airbnb Rental Income: $2824 Traditional Rental Income: $3303 Airbnb ROI: -2.13% Traditional ROI: -1.51%
5229 W Carmen Ave Chicago, IL 5229 W Carmen Ave, Chicago, IL 60630 \| Single Family Residential	3 beds \| 2 baths \| 1,394 sq.ft.	$485,000	Airbnb cash on cash: -2.32% Traditional cash on cash: 1.21% Airbnb Rental Income: $844 Traditional Rental Income: $2117 Airbnb ROI: -2.32% Traditional ROI: 1.21%
1938 N Hudson Ave Chicago, IL 1938 N Hudson Ave, Chicago, IL 60614 \| Single Family Residential	5 beds \| 5 baths \| 5,849 sq.ft.	$2,850,000	Airbnb cash on cash: -2.5% Traditional cash on cash: -1.46% Airbnb Rental Income: $2765 Traditional Rental Income: $4865 Airbnb ROI: -2.5% Traditional ROI: -1.46%
222 N Columbus Dr #3103 Chicago, IL Stunning 31st-floor 2-bedroom, 2-bath residence at Park Millennium, offering breathtaking ...	2 beds \| 2 baths \| 1,225 sq.ft.	$399,000	Airbnb cash on cash: -4% Traditional cash on cash: 0.08% Airbnb Rental Income: $1486 Traditional Rental Income: $2575 Airbnb ROI: -4% Traditional ROI: 0.08%
130 N Garland Ct #3702 Chicago, IL Stunning high-floor condo with awesome views of city & sunsets from floor-to-ceiling windo...	3 beds \| 2 baths \| 1,653 sq.ft.	$730,000	Airbnb cash on cash: -3.51% Traditional cash on cash: -0.74% Airbnb Rental Income: $1617 Traditional Rental Income: $3043 Airbnb ROI: -3.51% Traditional ROI: -0.74%
1645 W Ogden Ave #530 Chicago, IL RARELY AVAILABLE spacious 3 bed 2 bath loft with soaring 14' ceilings located in the West ...	3 beds \| 2 baths \| 1,415 sq.ft.	$485,000	Airbnb cash on cash: -3.41% Traditional cash on cash: 0.07% Airbnb Rental Income: $1047 Traditional Rental Income: $2264 Airbnb ROI: -3.41% Traditional ROI: 0.07%
5602 N Fairview Ave Chicago, IL 5602 N Fairview Ave, Chicago, IL 60631 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$475,000	Airbnb cash on cash: -2.02% Traditional cash on cash: -1.05% Airbnb Rental Income: $993 Traditional Rental Income: $1070 Airbnb ROI: -2.02% Traditional ROI: -1.05%
1432 W Chase Ave Chicago, IL 1432 W Chase Ave, Chicago, IL 60626 \| Single Family Residential	4 beds \| 2 baths \| 2,046 sq.ft.	$600,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 0.63% Airbnb Rental Income: $1439 Traditional Rental Income: $2269 Airbnb ROI: -1.62% Traditional ROI: 0.63%
9100 S Wallace St Chicago, IL Welcome to 9100 S Wallace - a beautifully renovated 3-bedroom, 3-bathroom home offering mo...	3 beds \| 3 baths \| 1,312 sq.ft.	$289,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 5.05% Airbnb Rental Income: $1275 Traditional Rental Income: $1900 Airbnb ROI: 1.28% Traditional ROI: 5.05%
9020 S Carpenter St Chicago, IL COME TAKE A LOOK AT THIS BEAUTIFUL NEWLY REMODELED 4 BEDROOM 2 BATH HOME IN WASHINGTON HEI...	3 beds \| 2 baths \| 1,400 sq.ft.	$225,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 6.28% Airbnb Rental Income: $1245 Traditional Rental Income: $1757 Airbnb ROI: 2.01% Traditional ROI: 6.28%
7216 S Central Park Ave Chicago, IL Well-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi...	4 beds \| 2 baths \| 1,080 sq.ft.	$290,000	Airbnb cash on cash: -1.39% Traditional cash on cash: 6.32% Airbnb Rental Income: $543 Traditional Rental Income: $2371 Airbnb ROI: -1.39% Traditional ROI: 6.32%
2854 S Central Park Ave Chicago, IL 2854 S Central Park Ave, Chicago, IL 60623 \| Single Family Residential	5 beds \| 2 baths \| 896 sq.ft.	$348,500	Airbnb cash on cash: 0.55% Traditional cash on cash: 3.07% Airbnb Rental Income: $1419 Traditional Rental Income: $1819 Airbnb ROI: 0.55% Traditional ROI: 3.07%
4836 S Dorchester Ave Chicago, IL Stunning 3-Flat Georgian Style Multi-Family Building in the Hyde Park/Kenwood Community, w...	7 beds \| 3 baths \| N/A	$950,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 0.59% Airbnb Rental Income: $1028 Traditional Rental Income: $2659 Airbnb ROI: -1.66% Traditional ROI: 0.59%
5029 S Dorchester Ave Chicago, IL	5 beds \| 4 baths \| 3,460 sq.ft.	$1,295,000	Airbnb cash on cash: -1.54% Traditional cash on cash: -0.49% Airbnb Rental Income: $2824 Traditional Rental Income: $3431 Airbnb ROI: -1.54% Traditional ROI: -0.49%
1932 W Crystal St #1 Chicago, IL 1932 W Crystal St #1, Chicago, IL 60622 \| Condo/Coop	3 beds \| 2 baths \| 2,100 sq.ft.	$699,900	Airbnb cash on cash: -2.65% Traditional cash on cash: 0.41% Airbnb Rental Income: $1057 Traditional Rental Income: $2694 Airbnb ROI: -2.65% Traditional ROI: 0.41%
6816 W 65th St #5 Chicago, IL 6816 W 65th St #5, Chicago, IL 60638 \| Townhouse	3 beds \| 2 baths \| 1,850 sq.ft.	$379,900	Airbnb cash on cash: -2.21% Traditional cash on cash: 2.26% Airbnb Rental Income: $1074 Traditional Rental Income: $2300 Airbnb ROI: -2.21% Traditional ROI: 2.26%
3553 W Sunnyside Ave #1 Chicago, IL 3553 W Sunnyside Ave #1, Chicago, IL 60625 \| Condo/Coop	1 beds \| 1 baths \| 725 sq.ft.	$164,900	Airbnb cash on cash: -4.39% Traditional cash on cash: 1.74% Airbnb Rental Income: $695 Traditional Rental Income: $1355 Airbnb ROI: -4.39% Traditional ROI: 1.74%
5814 S Massasoit Ave Chicago, IL 5814 S Massasoit Ave, Chicago, IL 60638 \| Single Family Residential	3 beds \| 1 baths \| 1,017 sq.ft.	$349,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 1.49% Airbnb Rental Income: $1115 Traditional Rental Income: $1643 Airbnb ROI: -1.27% Traditional ROI: 1.49%
2645 W Haddon Ave #2 Chicago, IL 2645 W Haddon Ave #2, Chicago, IL 60622 \| Condo/Coop	2 beds \| 2 baths \| 1,200 sq.ft.	$439,900	Airbnb cash on cash: -2.61% Traditional cash on cash: 1.26% Airbnb Rental Income: $920 Traditional Rental Income: $2169 Airbnb ROI: -2.61% Traditional ROI: 1.26%
130 S Canal St #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%
3214 S Canal St Chicago, IL 3214 S Canal St, Chicago, IL 60616 \| Single Family Residential	5 beds \| 5 baths \| 8,800 sq.ft.	$1,850,000	Airbnb cash on cash: -2.71% Traditional cash on cash: -0.44% Airbnb Rental Income: $1476 Traditional Rental Income: $4939 Airbnb ROI: -2.71% Traditional ROI: -0.44%
1211 S Prairie Ave #3401 Chicago, IL 1211 S Prairie Ave #3401, Chicago, IL 60605 \| Condo/Coop	3 beds \| 3 baths \| 2,920 sq.ft.	$1,490,000	Airbnb cash on cash: -5.13% Traditional cash on cash: -2.86% Airbnb Rental Income: $598 Traditional Rental Income: $3455 Airbnb ROI: -5.13% Traditional ROI: -2.86%
1345 S Wabash Ave #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%
840 N Lake Shore Dr #201 Chicago, IL 840 N Lake Shore Dr #201, Chicago, IL 60611 \| Condo/Coop	3 beds \| 3 baths \| 3,985 sq.ft.	$2,795,000	Airbnb cash on cash: -4.78% Traditional cash on cash: -4.37% Airbnb Rental Income: $2260 Traditional Rental Income: $2747 Airbnb ROI: -4.78% Traditional ROI: -4.37%
474 N Lake Shore Dr #2212 Chicago, IL Come see this once in a lifetime Chicago Condo. This home has been upgraded with wood lam...	N/A beds \| 1 baths \| 700 sq.ft.	$238,900	Airbnb cash on cash: -3.81% Traditional cash on cash: -3.4% Airbnb Rental Income: $882 Traditional Rental Income: $638 Airbnb ROI: -3.81% Traditional ROI: -3.4%
4824 S Kildare Ave Chicago, IL The opportunity to own one of the most traditional home in the history of architecture in ...	4 beds \| 2 baths \| N/A	$355,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 4.94% Airbnb Rental Income: $859 Traditional Rental Income: $2383 Airbnb ROI: -0.63% Traditional ROI: 4.94%
3301 N Ozanam Ave Chicago, IL 3301 N Ozanam Ave, Chicago, IL 60634 \| Multi Family	5 beds \| 3 baths \| N/A	$500,000	Airbnb cash on cash: -2.12% Traditional cash on cash: 2.69% Airbnb Rental Income: $973 Traditional Rental Income: $2870 Airbnb ROI: -2.12% Traditional ROI: 2.69%
1936 N Wilmot Ave Chicago, IL 1936 N Wilmot Ave, Chicago, IL 60647 \| Single Family Residential	6 beds \| 5 baths \| 6,300 sq.ft.	$3,499,999	Airbnb cash on cash: -3% Traditional cash on cash: -1.77% Airbnb Rental Income: $1356 Traditional Rental Income: $4946 Airbnb ROI: -3% Traditional ROI: -1.77%
1700 E 56th St #2809 Chicago, IL 1700 E 56th St #2809, Chicago, IL 60637 \| Condo/Coop	2 beds \| 2 baths \| 1,250 sq.ft.	$339,900	Airbnb cash on cash: -5.44% Traditional cash on cash: -0.73% Airbnb Rental Income: $970 Traditional Rental Income: $2122 Airbnb ROI: -5.44% Traditional ROI: -0.73%
1060 W Hollywood Ave #502 Chicago, IL 1060 W Hollywood Ave #502, Chicago, IL 60660 \| Condo/Coop	1 beds \| 1 baths \| 700 sq.ft.	$185,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 1.19% Airbnb Rental Income: $1322 Traditional Rental Income: $1252 Airbnb ROI: -0.74% Traditional ROI: 1.19%
5809 S Sangamon St Chicago, IL 5809 S Sangamon St, Chicago, IL 60621 \| Single Family Residential	6 beds \| 2 baths \| 1,687 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $2040 Airbnb ROI: N/A Traditional ROI: 5.01%

Real Estate investment in Chicago, IL

There are 4,550 properties for sale in the city of Chicago . The median list price in Chicago is $349,000 and the average price per square foot is $194. In March 2026, the average monthly cash on cash return in Chicago is 2.00%. The average monthly rental income in Chicago is $2,019.

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

There are 4,550 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 $2,019.

Your search for investment property begins and ends here

Investment Property for Sale in Chicago, IL

13223 S Buffalo Ave

Chicago, IL

3 beds | 2 baths | 1,100 sq.ft.

$199,000

Airbnb cash on cash: 0.53%

Traditional cash on cash: 7.5%

Airbnb Rental Income: $898

Traditional Rental Income: $1876

Airbnb ROI: 0.53%

Traditional ROI: 7.5%

13210 S Carondolet Ave

Chicago, IL

2 beds | 2 baths | 1,700 sq.ft.

$239,900

Airbnb cash on cash: -2.21%

Traditional cash on cash: 5.28%

Airbnb Rental Income: $617

Traditional Rental Income: $2024

Airbnb ROI: -2.21%

Traditional ROI: 5.28%

11616 S Harvard Ave

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 St

Chicago, IL

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

$240,000

Airbnb cash on cash: -0.21%

Traditional cash on cash: 8.19%

Airbnb Rental Income: $708

Traditional Rental Income: $2306

Airbnb ROI: -0.21%

Traditional ROI: 8.19%

4131 W Belmont Ave #402

Chicago, IL

2 beds | 2 baths | 1,102 sq.ft.

$375,000

Airbnb cash on cash: -3.09%

Traditional cash on cash: 1%

Airbnb Rental Income: $1082

Traditional Rental Income: $2152

Airbnb ROI: -3.09%

Traditional ROI: 1%

5130 S Menard Ave

Chicago, IL

3 beds | 1 baths | 945 sq.ft.

$290,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $1115

Traditional Rental Income: $1551

Airbnb ROI: -0.87%

Traditional ROI: 2.1%

5801 S Blackstone Ave

Chicago, IL

5 beds | 4 baths | 3,919 sq.ft.

$1,975,000

Airbnb cash on cash: -2.13%

Traditional cash on cash: -1.51%

Airbnb Rental Income: $2824

Traditional Rental Income: $3303

Airbnb ROI: -2.13%

Traditional ROI: -1.51%

5229 W Carmen Ave

Chicago, IL

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

$485,000

Airbnb cash on cash: -2.32%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $844

Traditional Rental Income: $2117

Airbnb ROI: -2.32%