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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
13223 S Buffalo AvenueChicago, ILWelcome to Hegewisch - a warm, close-knit Chicago neighborhood known for its small-town fe... |
3 beds | 2 baths | 1,100 sq.ft. |
$189,900 |
Airbnb cash on cash: 5.96%
|
5701 N Sheridan Road #3EChicago, ILBright, beautifully maintained 1-bedroom with sweeping lake and skyline views in the highl... |
1 beds | 1 baths | 850 sq.ft. |
$179,000 |
Airbnb cash on cash: 1.77%
|
6631 N Caldwell AvenueChicago, ILCHARM ABOUNDS IN THIS LOVINGLY MAINTAINED BRICK CAPE COD IN THE HIGHLY SOUGHT AFTER EDGEBR... |
3 beds | 3 baths | 1,545 sq.ft. |
$599,900 |
Airbnb cash on cash: -0.09%
|
5400 S HARPER Avenue #402Chicago, ILExperience the best of Hyde Park living in this beautifully maintained 2-bedroom, 1-bath c... |
2 beds | 1 baths | 900 sq.ft. |
$245,000 |
Airbnb cash on cash: -0.57%
|
5300 South Shore Drive #63Chicago, ILHigh floor, great views, very quiet! Thick concrete floors and ceilings. 10 windows in the... |
2 beds | 2 baths | 1,500 sq.ft. |
$149,900 |
Airbnb cash on cash: -2.72%
|
3730 W 111th Street #202Chicago, ILWelcome to this beautiful condo in the heart of Mt. Greenwood, where comfort, style, and a... |
2 beds | 2 baths | 1,350 sq.ft. |
$319,999 |
Airbnb cash on cash: 1.48%
|
2646 E 77th StreetChicago, ILWelcome home to this beautifully appointed (3) Bedroom (3.5) Bath residence where generous... |
3 beds | 4 baths | 1,789 sq.ft. |
$275,000 |
Airbnb cash on cash: 2.94%
|
7363 South Shore Drive #508Chicago, ILInvestor special! This 1-bedroom, 1-bath condo offers an excellent opportunity for buyers ... |
1 beds | 1 baths | 800 sq.ft. |
$50,000 |
Airbnb cash on cash: 4.19%
|
841 W Belle Plaine Avenue #3Chicago, ILWow! Must see this unique, spacious top-floor 2-bedroom, 1.5-bath vintage condo in desirab... |
2 beds | 2 baths | 1,482 sq.ft. |
$389,500 |
Airbnb cash on cash: -0.48%
|
707 W GORDON TerraceChicago, ILWelcome to 707 W Gordon Terrace, a striking single-family residence that blends timeless e... |
4 beds | 4 baths | N/A |
$2,100,000 |
Airbnb cash on cash: -1.27%
|
9020 S Carpenter StreetChicago, ILWelcome to this nicely updated home offering the perfect combination of comfort, style, an... |
3 beds | 2 baths | 1,400 sq.ft. |
$205,000 |
Airbnb cash on cash: 4.52%
|
2035 W Division Street #3Chicago, ILWelcome to this spacious 2-bedroom, 2-bathroom home in the heart of Wicker Park, offering ... |
2 beds | 2 baths | 1,500 sq.ft. |
$549,999 |
Airbnb cash on cash: -0.54%
|
6562 N Damen AvenueChicago, ILWelcome to this two-story, 3-bedroom 2-bath home with a finished basement and 2-car garage... |
3 beds | 2 baths | 1,769 sq.ft. |
$470,000 |
Airbnb cash on cash: 2.2%
|
4836 S Dorchester AvenueChicago, ILLooking for a Stunning 3-Flat Georgian Style Multi-Family Building or convert to your Sing... |
6 beds | 5 baths | N/A |
$925,000 |
Airbnb cash on cash: 0.14%
|
6816 W 65th Street #5Chicago, ILBeautifully up-kept townhouse in the Chicago land area. Home offers natural light througho... |
3 beds | 3 baths | 1,850 sq.ft. |
$369,900 |
Airbnb cash on cash: 1.82%
|
1514 W Victoria Street #2Chicago, ILHere is your chance to beat next year's spring market! This fine 2 bedroom, 2 bathroom And... |
2 beds | 2 baths | N/A |
$480,000 |
Airbnb cash on cash: 1.27%
|
2651 W MEDILL AvenueChicago, ILMODERN DESIGN, EXCEPTIONAL LIVING SPACE, AND BEAUTIFULLY FINISHED OUTDOOR RETREATS come to... |
4 beds | 4 baths | 3,279 sq.ft. |
$1,595,000 |
Airbnb cash on cash: -0.41%
|
1647 W Sherwin Avenue #1Chicago, ILSpacious 3 bedroom, 2 bath duplex down condo in Rogers Park! Featuring hardwood floors, gr... |
3 beds | 2 baths | N/A |
$265,000 |
Airbnb cash on cash: 1.88%
|
1901 S Calumet Avenue #1510Chicago, ILWelcome to Harbor View in the heart of Chicago's South Loop! This beautifully updated 1-be... |
1 beds | 1 baths | 830 sq.ft. |
$318,900 |
Airbnb cash on cash: 1.18%
|
801 S Plymouth Court #906Chicago, ILBright and airy one-bedroom in the heart of Printers Row, featuring an open-concept layout... |
1 beds | 1 baths | N/A |
$175,000 |
Airbnb cash on cash: 1.57%
|
1901 S Calumet Avenue #1312Chicago, IL
|
2 beds | 2 baths | N/A |
$420,000 |
Airbnb cash on cash: -1.71%
|
1345 S Wabash Avenue #408Chicago, IL
|
1 beds | 1 baths | 728 sq.ft. |
$250,000 |
Airbnb cash on cash: 1.39%
|
840 N Lake Shore Drive #201Chicago, ILEnjoy the unobstructed views of the lakefront and the park in the world class Lucian Lagra... |
3 beds | 4 baths | 3,985 sq.ft. |
$2,395,000 |
Airbnb cash on cash: -3.11%
|
9112 S Aberdeen StreetChicago, ILWelcome to this charming Chicago home featuring comfortable living spaces, a functional la... |
4 beds | 3 baths | 3,720 sq.ft. |
$334,900 |
Airbnb cash on cash: 3.22%
|
1343 W 31st Street #1Chicago, ILWelcome to this beautifully updated and spacious partially below- grade first-floor Bridge... |
3 beds | 1 baths | 1,300 sq.ft. |
$269,900 |
Airbnb cash on cash: 4.05%
|
4839 S Vincennes Avenue #1Chicago, ILDo you need space? Look no further! Welcome to this beautiful 4 beds/3 full baths duplex-d... |
4 beds | 3 baths | 2,500 sq.ft. |
$399,900 |
Airbnb cash on cash: 2.09%
|
544 E 46th PlaceChicago, ILNewer-construction single-family home on a tree-lined block in Bronzeville. Thoughtfully d... |
5 beds | 4 baths | 3,000 sq.ft. |
$649,900 |
Airbnb cash on cash: 1.24%
|
4818 S Evans AvenueChicago, ILWelcome home to this beautifully renovated 5-bedroom, 3.5-bathroom Greystone. Fully rebuil... |
5 beds | 4 baths | 3,800 sq.ft. |
$850,000 |
Airbnb cash on cash: -0.06%
|
1325 N Astor Street #2Chicago, ILA rare offering in one of Chicago's most distinguished residential buildings, this expansi... |
3 beds | 4 baths | 4,300 sq.ft. |
$1,600,000 |
Airbnb cash on cash: -3.25%
|
Real Estate investment in Chicago, IL
There are 3,733 properties for sale in the city of Chicago . The median list price in Chicago is $409,805 and the average price per square foot is $239. In November 2026, the average monthly cash on cash return in Chicago is 2.00%. The average monthly rental income in Chicago is $2,131.