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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2610 W 80th St Chicago, IL 2610 W 80th St, Chicago, IL 60652 \| Single Family Residential	2 beds \| 1 baths \| 855 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.99% Airbnb Rental Income: $null Traditional Rental Income: $1328 Airbnb ROI: N/A Traditional ROI: 1.99%
1722 N Keeler Avenue Chicago, IL Hot Hermosa location! Updated single family home on a great block. House went through ext...	3 beds \| 1 baths \| 842 sq.ft.	$299,950	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $1632 Airbnb ROI: N/A Traditional ROI: 3.56%
60 E Monroe St #2001 Chicago, IL 60 E Monroe St #2001, Chicago, IL 60603 \| Condo/Coop	3 beds \| 2 baths \| 1,750 sq.ft.	$1,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.56% Airbnb Rental Income: $null Traditional Rental Income: $2745 Airbnb ROI: N/A Traditional ROI: -2.56%
1160 S Michigan Ave #2502 Chicago, IL 1160 S Michigan Ave #2502, Chicago, IL 60605 \| Condo/Coop	2 beds \| 2 baths \| 1,231 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.59% Airbnb Rental Income: $null Traditional Rental Income: $2449 Airbnb ROI: N/A Traditional ROI: 0.59%
1528 W Monroe St #200 Chicago, IL 1528 W Monroe St #200, Chicago, IL 60607 \| Condo/Coop	3 beds \| 2 baths \| 1,550 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.11% Airbnb Rental Income: $null Traditional Rental Income: $2512 Airbnb ROI: N/A Traditional ROI: 0.11%
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.	$387,546	Airbnb cash on cash: N/A Traditional cash on cash: 1.5% Airbnb Rental Income: $null Traditional Rental Income: $1819 Airbnb ROI: N/A Traditional ROI: 1.5%
4836 S Dorchester Avenue Chicago, IL Stunning 3-Flat Georgian Style Multi-Family Building in the Hyde Park/Kenwood Community, w...	6 beds \| N/A baths \| N/A	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.55% Airbnb Rental Income: $null Traditional Rental Income: $2659 Airbnb ROI: N/A Traditional ROI: 0.55%
8151 S Bennett Avenue Chicago, IL This expansive brick 2-flat offers versatile living across three fully finished levels. En...	9 beds \| N/A baths \| N/A	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.21% Airbnb Rental Income: $null Traditional Rental Income: $2779 Airbnb ROI: N/A Traditional ROI: 9.21%
5455 N Sheridan Rd #1904 Chicago, IL 5455 N Sheridan Rd #1904, Chicago, IL 60640 \| Condo/Coop	2 beds \| 1 baths \| 850 sq.ft.	$299,990	Airbnb cash on cash: N/A Traditional cash on cash: -1.66% Airbnb Rental Income: $null Traditional Rental Income: $1529 Airbnb ROI: N/A Traditional ROI: -1.66%
5814 S Massasoit Ave Chicago, IL 5814 S Massasoit Ave, Chicago, IL 60638 \| Single Family Residential	3 beds \| 1 baths \| 1,017 sq.ft.	$359,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.35% Airbnb Rental Income: $null Traditional Rental Income: $1643 Airbnb ROI: N/A Traditional ROI: 1.35%
3214 S Canal St Chicago, IL 3214 S Canal St, Chicago, IL 60616 \| Single Family Residential	5 beds \| 5 baths \| 8,800 sq.ft.	$1,849,999	Airbnb cash on cash: N/A Traditional cash on cash: -0.44% Airbnb Rental Income: $null Traditional Rental Income: $4939 Airbnb ROI: N/A Traditional ROI: -0.44%
175 E Delaware Place #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.	$720,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.79% Airbnb Rental Income: $null Traditional Rental Income: $2363 Airbnb ROI: N/A Traditional ROI: -1.79%
9101 S Racine Ave Chicago, IL 9101 S Racine Ave, Chicago, IL 60620 \| Single Family Residential	4 beds \| 3 baths \| 2,800 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.05% Airbnb Rental Income: $null Traditional Rental Income: $3104 Airbnb ROI: N/A Traditional ROI: 6.05%
544 E 46th Pl Chicago, IL 544 E 46th Pl, Chicago, IL 60653 \| Single Family Residential	5 beds \| 3 baths \| 3,000 sq.ft.	$760,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.25% Airbnb Rental Income: $null Traditional Rental Income: $3288 Airbnb ROI: N/A Traditional ROI: 1.25%
4531 S Lawler Avenue Chicago, IL Pristine 3bed/2bath raised ranch ready for move-in. Spacious layout with finished baseme...	3 beds \| 2 baths \| 1,008 sq.ft.	$309,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.36% Airbnb Rental Income: $null Traditional Rental Income: $1920 Airbnb ROI: N/A Traditional ROI: 4.36%
2650 N Lakeview Ave #3101 Chicago, IL 2650 N Lakeview Ave #3101, Chicago, IL 60614 \| Condo/Coop	2 beds \| 2 baths \| 1,250 sq.ft.	$519,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.36% Airbnb Rental Income: $null Traditional Rental Income: $2213 Airbnb ROI: N/A Traditional ROI: -1.36%
1720 N Mohawk St Chicago, IL 1720 N Mohawk St, Chicago, IL 60614 \| Single Family Residential	6 beds \| 5 baths \| 5,900 sq.ft.	$4,095,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.95% Airbnb Rental Income: $null Traditional Rental Income: $5071 Airbnb ROI: N/A Traditional ROI: -1.95%
1205 W 97th Pl Chicago, IL 1205 W 97th Pl, Chicago, IL 60643 \| Single Family Residential	5 beds \| 2 baths \| 3,308 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2242 Airbnb ROI: N/A Traditional ROI: 4.37%
545 N Dearborn St #3601 Chicago, IL 545 N Dearborn St #3601, Chicago, IL 60654 \| Condo/Coop	3 beds \| 2 baths \| 2,500 sq.ft.	$1,149,000	Airbnb cash on cash: N/A Traditional cash on cash: -3.59% Airbnb Rental Income: $null Traditional Rental Income: $2863 Airbnb ROI: N/A Traditional ROI: -3.59%
1112 N Dearborn St #1 Chicago, IL 1112 N Dearborn St #1, Chicago, IL 60610 \| Condo/Coop	2 beds \| 2 baths \| 2,255 sq.ft.	$1,395,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.19% Airbnb Rental Income: $null Traditional Rental Income: $2743 Airbnb ROI: N/A Traditional ROI: -2.19%
405 N Wabash Ave #4308 Chicago, IL 405 N Wabash Ave #4308, Chicago, IL 60611 \| Condo/Coop	4 beds \| 4 baths \| 3,100 sq.ft.	$1,195,000	Airbnb cash on cash: N/A Traditional cash on cash: -3.36% Airbnb Rental Income: $null Traditional Rental Income: $3966 Airbnb ROI: N/A Traditional ROI: -3.36%
6005 W Waveland Ave Chicago, IL 6005 W Waveland Ave, Chicago, IL 60634 \| Single Family Residential	7 beds \| 3 baths \| 2,769 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.53% Airbnb Rental Income: $null Traditional Rental Income: $3333 Airbnb ROI: N/A Traditional ROI: 2.53%
7927 S BURNHAM Avenue Chicago, IL Possible FHA/VA Financing * We are in the area covered by the Cook County DP Assistance Pr...	2 beds \| 2 baths \| 1,124 sq.ft.	$190,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.66% Airbnb Rental Income: $null Traditional Rental Income: $1775 Airbnb ROI: N/A Traditional ROI: 7.66%
8434 S Yates Blvd Chicago, IL 8434 S Yates Blvd, Chicago, IL 60617 \| Single Family Residential	4 beds \| 3 baths \| 1,700 sq.ft.	$305,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.39% Airbnb Rental Income: $null Traditional Rental Income: $2571 Airbnb ROI: N/A Traditional ROI: 5.39%
7412 S Phillips Ave Chicago, IL	4 beds \| 2 baths \| 2,328 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.98% Airbnb Rental Income: $null Traditional Rental Income: $2408 Airbnb ROI: N/A Traditional ROI: 4.98%
60 E Monroe St #5103 Chicago, IL 60 E Monroe St #5103, Chicago, IL 60603 \| Condo/Coop	2 beds \| 2 baths \| 1,500 sq.ft.	$719,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.74% Airbnb Rental Income: $null Traditional Rental Income: $2744 Airbnb ROI: N/A Traditional ROI: -1.74%
310 S Michigan Ave #1907 Chicago, IL 310 S Michigan Ave #1907, Chicago, IL 60604 \| Condo/Coop	2 beds \| 2 baths \| 1,350 sq.ft.	$489,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.04% Airbnb Rental Income: $null Traditional Rental Income: $2344 Airbnb ROI: N/A Traditional ROI: -0.04%
7017 S Hermitage Avenue Chicago, IL Come and view your new home today in the heart of West Englewood! This fully insulated re...	5 beds \| 3 baths \| 1,148 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $1962 Airbnb ROI: N/A Traditional ROI: 3.82%
6619 S Ellis Ave Chicago, IL 6619 S Ellis Ave, Chicago, IL 60637 \| Single Family Residential	4 beds \| 2 baths \| 2,929 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.92% Airbnb Rental Income: $null Traditional Rental Income: $2255 Airbnb ROI: N/A Traditional ROI: 5.92%
4757 S Langley Ave Chicago, IL 4757 S Langley Ave, Chicago, IL 60615 \| Single Family Residential	4 beds \| 2 baths \| 2,520 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $2357 Airbnb ROI: N/A Traditional ROI: 1.6%
212 W Washington St #1807 Chicago, IL 212 W Washington St #1807, Chicago, IL 60606 \| Condo/Coop	4 beds \| 4 baths \| 2,300 sq.ft.	$800,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.44% Airbnb Rental Income: $null Traditional Rental Income: $3867 Airbnb ROI: N/A Traditional ROI: -1.44%
34 E BELLEVUE Place Chicago, IL Quintessentially old Chicago on the outside and exquisitely modern on the inside, 34 E. Be...	5 beds \| 7 baths \| 6,500 sq.ft.	$3,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.19% Airbnb Rental Income: $null Traditional Rental Income: $6280 Airbnb ROI: N/A Traditional ROI: -1.19%
1242 N Lake Shore Dr #22 Chicago, IL 1242 N Lake Shore Dr #22, Chicago, IL 60610 \| Condo/Coop	4 beds \| 3 baths \| 4,200 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: -5.67% Airbnb Rental Income: $null Traditional Rental Income: $3046 Airbnb ROI: N/A Traditional ROI: -5.67%
1041 N Ridgeway Ave Chicago, IL 1041 N Ridgeway Ave, Chicago, IL 60651 \| Single Family Residential	4 beds \| 2 baths \| 2,200 sq.ft.	$239,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.05% Airbnb Rental Income: $null Traditional Rental Income: $2642 Airbnb ROI: N/A Traditional ROI: 8.05%
1823 N Bissell St Chicago, IL 1823 N Bissell St, Chicago, IL 60614 \| Single Family Residential	6 beds \| 5 baths \| N/A	$3,300,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.63% Airbnb Rental Income: $null Traditional Rental Income: $5082 Airbnb ROI: N/A Traditional ROI: -1.63%
1901 S CALUMET Avenue #2712 Chicago, IL Enjoy stunning, unobstructed city views from every room and the private balcony of this 2 ...	2 beds \| 2 baths \| 1,070 sq.ft.	$405,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.29% Airbnb Rental Income: $null Traditional Rental Income: $2112 Airbnb ROI: N/A Traditional ROI: -0.29%

Real Estate investment in Chicago, IL

There are 3,097 properties for sale in the city of Chicago . The median list price in Chicago is $333,000 and the average price per square foot is $188. In December 2025, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,139.

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

There are 3,097 investment properties available for sale in Chicago.

In 2025, the best neighborhood to buy investment property is South Shore.

The ROI for Short-Term is higher than the Long-Term in Chicago with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Chicago, IL

2610 W 80th St

Chicago, IL

2 beds | 1 baths | 855 sq.ft.

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.99%

Airbnb Rental Income: $null

Traditional Rental Income: $1328

Airbnb ROI: N/A

Traditional ROI: 1.99%

1722 N Keeler Avenue

Chicago, IL

3 beds | 1 baths | 842 sq.ft.

$299,950

Airbnb cash on cash: N/A

Traditional cash on cash: 3.56%

Airbnb Rental Income: $null

Traditional Rental Income: $1632

Airbnb ROI: N/A

Traditional ROI: 3.56%

60 E Monroe St #2001

Chicago, IL

3 beds | 2 baths | 1,750 sq.ft.

$1,000,000

Airbnb cash on cash: N/A

Traditional cash on cash: -2.56%

Airbnb Rental Income: $null

Traditional Rental Income: $2745

Airbnb ROI: N/A

Traditional ROI: -2.56%

1160 S Michigan Ave #2502

Chicago, IL

2 beds | 2 baths | 1,231 sq.ft.

$415,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.59%

Airbnb Rental Income: $null

Traditional Rental Income: $2449

Airbnb ROI: N/A

Traditional ROI: 0.59%

1528 W Monroe St #200

Chicago, IL

3 beds | 2 baths | 1,550 sq.ft.

$585,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.11%

Airbnb Rental Income: $null

Traditional Rental Income: $2512

Airbnb ROI: N/A

Traditional ROI: 0.11%

2854 S Central Park Ave

Chicago, IL

5 beds | 2 baths | 896 sq.ft.

$387,546

Airbnb cash on cash: N/A

Traditional cash on cash: 1.5%

Airbnb Rental Income: $null

Traditional Rental Income: $1819

Airbnb ROI: N/A

Traditional ROI: 1.5%

4836 S Dorchester Avenue

Chicago, IL

6 beds | N/A baths | N/A

$975,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.55%

Airbnb Rental Income: $null

Traditional Rental Income: $2659

Airbnb ROI: N/A

Traditional ROI: 0.55%

8151 S Bennett Avenue

Chicago, IL

9 beds | N/A baths | N/A

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.21%

Airbnb Rental Income: $null

Traditional Rental Income: $2779

Airbnb ROI: N/A