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 |
|---|---|---|---|
7240 S Oakley AvenueChicago, ILBRING YOUR CLIENTS! THIS BEAUTHY LOOKS LITTLE BUT IS ENORMOUS! WITH PLANE OF ROOMS IDEAL F... |
4 beds | 2 baths | 1,016 sq.ft. |
$318,990 |
Airbnb cash on cash: 1.75%
|
5121 S Central AveChicago, IL5121 S Central Ave, Chicago, IL 60638 | Single Family Residential |
3 beds | 2 baths | 900 sq.ft. |
$349,900 |
Airbnb cash on cash: -0.26%
|
1722 N Keeler AvenueChicago, ILHot Hermosa location! Updated single family home on a great block. House went through ext... |
3 beds | 1 baths | 842 sq.ft. |
$329,500 |
Airbnb cash on cash: 2.08%
|
5728 S Stony Island Ave #2Chicago, IL5728 S Stony Island Ave #2, Chicago, IL 60637 | Condo/Coop |
1 beds | 1 baths | 900 sq.ft. |
$105,000 |
Airbnb cash on cash: -4.66%
|
4141 N KEDZIE Avenue #307Chicago, ILCome see this stunning 2 bed / 2 bath condo loaded with upgrades! Step inside to a bright,... |
2 beds | 2 baths | 1,691 sq.ft. |
$424,900 |
Airbnb cash on cash: -0.87%
|
5151 W Winona StreetChicago, ILWelcome to this exquisite agent-owned residence located in the heart of Jefferson Park. Th... |
5 beds | 3 baths | N/A |
$775,000 |
Airbnb cash on cash: 0.5%
|
1919 N Kenmore Avenue #1Chicago, ILTucked into the heart of Lincoln Park on a picturesque, tree-lined street, this masterfull... |
3 beds | 3 baths | N/A |
$890,000 |
Airbnb cash on cash: -0.75%
|
40 E 9th Street #1516Chicago, ILDiscover a unique gem within the South Loop's prominent high-rise community-a stunning thr... |
3 beds | 3 baths | 2,000 sq.ft. |
$400,000 |
Airbnb cash on cash: -3.49%
|
6929 S Loomis BoulevardChicago, ILThis house has everything your client requested. 5 bedrooms, 3 full bathrooms, Full finis... |
4 beds | 3 baths | 1,000 sq.ft. |
$259,900 |
Airbnb cash on cash: 2.16%
|
7216 S CENTRAL PARK AvenueChicago, ILWell-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi... |
3 beds | 2 baths | N/A |
$315,300 |
Airbnb cash on cash: 0.27%
|
1620 W Huron Street #1Chicago, ILAll the top end amenities and three outdoor spaces in this first floor 2 bed, 2 bath condo... |
2 beds | 2 baths | 1,162 sq.ft. |
$490,000 |
Airbnb cash on cash: 0.02%
|
2423 W Erie StreetChicago, ILWelcome to your dream home in the highly desirable Smith Park neighborhood, crafted by acc... |
4 beds | 4 baths | N/A |
$999,000 |
Airbnb cash on cash: N/A
|
5151 W Fletcher StreetChicago, IL** Huge Price Reduction **Move right into this stunning, fully updated 6-bedroom, 3-bathro... |
4 beds | 3 baths | 3,450 sq.ft. |
$620,000 |
Airbnb cash on cash: 1.27%
|
6558 N Washtenaw Avenue #2Chicago, ILSpacious 3 bedroom, 2 bathroom condo with modern updates, washer/dryer in-unit and a priva... |
3 beds | 2 baths | 1,500 sq.ft. |
$297,000 |
Airbnb cash on cash: 1.31%
|
4836 S Dorchester AvenueChicago, ILStunning 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: -0.28%
|
2337 W Wolfram Street #411Chicago, ILSpacious 2-bedroom, 2-bath home in a modern elevator building surrounded by serene treetop... |
2 beds | 2 baths | N/A |
$420,000 |
Airbnb cash on cash: 0.07%
|
3036 N Luna AvenueChicago, ILSpacious & Stylish 5-Bedroom Home with Modern Upgrades! Welcome to your new home-offering... |
3 beds | 3 baths | 2,532 sq.ft. |
$535,000 |
Airbnb cash on cash: -0.21%
|
8151 S Bennett AvenueChicago, ILThis expansive brick 2-flat offers versatile living across three fully finished levels. En... |
9 beds | 3 baths | N/A |
$250,000 |
Airbnb cash on cash: 1.5%
|
11730 S Oakley AveChicago, IL11730 S Oakley Ave, Chicago, IL 60643 | Single Family Residential |
3 beds | 2 baths | 1,739 sq.ft. |
$369,990 |
Airbnb cash on cash: -0.01%
|
651 N Milwaukee Ave #302Chicago, IL651 N Milwaukee Ave #302, Chicago, IL 60642 | Condo/Coop |
2 beds | 2 baths | 1,274 sq.ft. |
$459,000 |
Airbnb cash on cash: -1.38%
|
1530 S State Street #620Chicago, ILBeautiful 1BR/1BA, true concrete loft in the historic Beatrice Cold Storage building with ... |
1 beds | 1 baths | N/A |
$299,000 |
Airbnb cash on cash: -0.89%
|
1211 S Prairie Avenue #3502Chicago, ILWelcome to luxury living at One Museum Park East! Experience breathtaking panoramic views... |
2 beds | 3 baths | 2,197 sq.ft. |
$1,350,000 |
Airbnb cash on cash: -2.81%
|
2730 N Magnolia AveChicago, IL2730 N Magnolia Ave, Chicago, IL 60614 | Single Family Residential |
6 beds | 6 baths | 6,200 sq.ft. |
$4,250,000 |
Airbnb cash on cash: -2.51%
|
1929 N Maud AvenueChicago, ILThis one is an undeniable showstopper! Blending architectural character with modern sophis... |
3 beds | 2 baths | 1,655 sq.ft. |
$995,000 |
Airbnb cash on cash: -0.43%
|
175 E Delaware Place #7204Chicago, ILWelcome 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: -2.65%
|
401 E Ontario Street #1805Chicago, ILLovely junior one bedroom in desirable Streeterville neighborhood located steps from the l... |
1 beds | 1 baths | 700 sq.ft. |
$265,000 |
Airbnb cash on cash: 0.7%
|
9356 S Union AveChicago, IL9356 S Union Ave, Chicago, IL 60628 | Single Family Residential |
3 beds | 2 baths | 1,097 sq.ft. |
$299,000 |
Airbnb cash on cash: 0.79%
|
1709 N Newland AveChicago, IL1709 N Newland Ave, Chicago, IL 60707 | Single Family Residential |
3 beds | 2 baths | 2,068 sq.ft. |
$599,900 |
Airbnb cash on cash: -0.94%
|
4531 S Lawler AvenueChicago, ILPristine 3bed/2bath raised ranch ready for move-in. Spacious layout with finished baseme... |
3 beds | 2 baths | 1,008 sq.ft. |
$329,000 |
Airbnb cash on cash: 1.53%
|
545 N Dearborn Street #1202Chicago, ILRenovated 850 sq. ft. 1BR at Grand Plaza in River North. Features hardwood floors, chef's ... |
1 beds | 1 baths | 850 sq.ft. |
$300,000 |
Airbnb cash on cash: -0.27%
|
21 E Huron Street #706Chicago, ILWhen Parisian charm meets New York Edge in the heart of Chicago - Unlike Anything You've S... |
2 beds | 2 baths | 1,771 sq.ft. |
$1,650,000 |
Airbnb cash on cash: -1.97%
|
630 N State Street #1406Chicago, ILBack on the market due to buyer unable to sell their property. Experience refined urban li... |
2 beds | 2 baths | 1,241 sq.ft. |
$485,000 |
Airbnb cash on cash: -1.6%
|
2 E Erie Street #1605Chicago, ILAn exceptional opportunity in the heart of River North-just steps from Michigan Avenue. Ev... |
3 beds | 3 baths | 2,082 sq.ft. |
$825,000 |
Airbnb cash on cash: -2.05%
|
401 E Ontario Street #809Chicago, ILLOCATION, LOCATION, LOCATION! This OVERSIZED CORNER unit with gorgeous city and lake views... |
2 beds | 2 baths | 1,200 sq.ft. |
$425,000 |
Airbnb cash on cash: -0.92%
|
2244 W IRVING PARK RoadChicago, ILPRIME CANDIDATE FOR OWNER OCCUPANT, FHA 203K BUYER! Single family home located in high tr... |
3 beds | 2 baths | N/A |
$624,900 |
Airbnb cash on cash: -0.13%
|
Real Estate investment in Chicago, IL
There are 3,956 properties for sale in the city of Chicago . The median list price in Chicago is $374,900 and the average price per square foot is $215. In September 2025, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,346.