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 |
|---|---|---|---|
7801 S Ada StreetChicago, ILWelcome 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: 0.1%
|
5918 S Albany AvenueChicago, ILGREAT 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: 1.54%
|
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. |
$199,000 |
Airbnb cash on cash: -0.01%
|
1709 NORTH PARK Avenue #1Chicago, ILThis charming vintage-chic condo blends classic character with thoughtful updates in a pri... |
2 beds | 2 baths | N/A |
$575,000 |
Airbnb cash on cash: -1.52%
|
1905 N Bissell Street #2Chicago, ILImpeccably designed resale from critically acclaimed PLD Development. This highly upgraded... |
3 beds | 2 baths | N/A |
$950,000 |
Airbnb cash on cash: -1.93%
|
801 S Plymouth Court #1111Chicago, ILRarely available Penthouse unit overlooking Sears Tower (Willis) and downtown Chicago. 2 l... |
2 beds | 2 baths | 1,300 sq.ft. |
$265,000 |
Airbnb cash on cash: -4.73%
|
8 W MONROE Street #1209Chicago, ILUnbeatable location in the heart of the Loop, with the Red and Blue train lines on the sam... |
2 beds | 2 baths | 990 sq.ft. |
$318,000 |
Airbnb cash on cash: -0.66%
|
1645 W Ogden Avenue #530Chicago, ILRarely available 3 bed, 2 bath loft in the West Loop with soaring 14' ceilings and oversiz... |
3 beds | 2 baths | 1,415 sq.ft. |
$485,000 |
Airbnb cash on cash: -3.55%
|
5555 N Cumberland Avenue #413Chicago, ILThis elegant high-rise residence offers a refined living experience in a prime location. S... |
2 beds | 2 baths | 1,700 sq.ft. |
$425,000 |
Airbnb cash on cash: -1.77%
|
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: N/A
|
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. |
$379,900 |
Airbnb cash on cash: -0.23%
|
832 N Washtenaw Avenue #3Chicago, ILPerched up above the neighborhood with privacy and natural light in every direction, welco... |
2 beds | 2 baths | N/A |
$560,000 |
Airbnb cash on cash: -1.63%
|
2334 W Ohio StreetChicago, ILSpectacular home on a 30' wide lot with amazing finishes throughout. Exclusive all-masonry... |
5 beds | 4 baths | 4,584 sq.ft. |
$1,950,000 |
Airbnb cash on cash: -2.37%
|
1211 S Prairie Avenue #3401Chicago, ILExperience 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: -4.96%
|
910 S Michigan Avenue #1009Chicago, IL
|
1 beds | 1 baths | N/A |
$255,000 |
Airbnb cash on cash: -2.88%
|
1345 S Wabash Avenue #408Chicago, ILWelcome 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: -2.71%
|
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. |
$2,745,000 |
Airbnb cash on cash: -4.34%
|
401 E Ontario Street #1410Chicago, ILWelcome to elevated city living at 401 E Ontario St - a beautifully positioned 14th-floor ... |
1 beds | 1 baths | 900 sq.ft. |
$338,000 |
Airbnb cash on cash: -4.11%
|
4824 S Kildare AvenueChicago, ILThe opportunity to own one of the most traditional home in the history of architecture in ... |
3 beds | 2 baths | N/A |
$345,000 |
Airbnb cash on cash: 0.23%
|
1210 N Astor Street #1BChicago, ILSet along the tree lined elegance of Astor Street in the heart of the Gold Coast, this rem... |
3 beds | 2 baths | 1,800 sq.ft. |
$850,000 |
Airbnb cash on cash: -5.22%
|
3740 N Pacific AvenueChicago, ILStep into this beautifully updated 5-bedroom, 3-bath raised ranch, offering nearly new-con... |
5 beds | 3 baths | 3,000 sq.ft. |
$575,000 |
Airbnb cash on cash: N/A
|
4840 S Dorchester Avenue #1Chicago, ILThe Dorchester Collection is an exclusive, newly constructed gated townhome community nest... |
3 beds | 3 baths | N/A |
$900,000 |
Airbnb cash on cash: -2.9%
|
8518 W Rascher Avenue #2Chicago, ILReady to move in now! This spacious, first-floor one-bedroom unit boasts a great location ... |
1 beds | 1 baths | N/A |
$165,000 |
Airbnb cash on cash: -1.31%
|
9328 S PAXTON AvenueChicago, IL
|
5 beds | 2 baths | N/A |
$289,000 |
Airbnb cash on cash: 1.4%
|
1742 N Bissell StreetChicago, ILSituated on one of the most prestigious streets in Lincoln Park, this brick three-story si... |
4 beds | 4 baths | N/A |
$1,350,000 |
Airbnb cash on cash: -1.25%
|
Real Estate investment in Chicago, IL
There are 3,347 properties for sale in the city of Chicago . The median list price in Chicago is $399,945 and the average price per square foot is $232. In May 2026, the average monthly cash on cash return in Chicago is 2.00%. The average monthly rental income in Chicago is $2,344.