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. |
$314,990 |
Airbnb cash on cash: N/A
|
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. |
$315,000 |
Airbnb cash on cash: 2.62%
|
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: -1.74%
|
7228 N Rogers AvenueChicago, ILThis is a 3 Bedroom, 1.5 Bath, 2 story, frame farm house with 1 Deeded Parking Space. It i... |
2 beds | 3 baths | 1,600 sq.ft. |
$435,000 |
Airbnb cash on cash: 0.79%
|
4343 N Clarendon Avenue #707Chicago, ILInvestors! Welcome to Buena Park. This incredible unit is a large one bedroom one bath wit... |
1 beds | 1 baths | 790 sq.ft. |
$139,900 |
Airbnb cash on cash: -2.19%
|
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. |
$255,900 |
Airbnb cash on cash: 0.61%
|
7216 S CENTRAL PARK AvenueChicago, ILWell-maintained brick ranch in move-in condition! Features gleaming hardwood floors, origi... |
3 beds | 2 baths | N/A |
$304,900 |
Airbnb cash on cash: 0.08%
|
7205 S HAMLIN AvenueChicago, ILMaintenance free 4 bedroom ranch with finished basement. 3 bedrooms on the main and one in... |
3 beds | 2 baths | 1,080 sq.ft. |
$379,900 |
Airbnb cash on cash: 1.45%
|
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: -0.17%
|
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: -0.36%
|
8151 S Bennett AvenueChicago, ILThis 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: 4.76%
|
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: -2.86%
|
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. |
$260,000 |
Airbnb cash on cash: 0.09%
|
3558 W Belle Plaine Avenue #3Chicago, ILBright and full of personality, this two-bedroom Irving Park condo offers stylish comfort ... |
2 beds | 1 baths | 1,000 sq.ft. |
$255,000 |
Airbnb cash on cash: 0.89%
|
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 |
$355,000 |
Airbnb cash on cash: 2.38%
|
9356 S Union AvenueChicago, ILBeautifully updated 3-bedroom, 2-bath brick ranch with a full finished basement. Ideally l... |
3 beds | 2 baths | 1,097 sq.ft. |
$275,000 |
Airbnb cash on cash: 1.78%
|
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. |
$309,000 |
Airbnb cash on cash: 1.33%
|
3916 W Grand AvenueChicago, ILMove in ready! This cozy single-family home has a lot to offer with three full bathrooms, ... |
3 beds | 3 baths | 900 sq.ft. |
$320,000 |
Airbnb cash on cash: 1.07%
|
11138 S Artesian AveChicago, IL11138 S Artesian Ave, Chicago, IL 60655 | Single Family Residential |
3 beds | 3 baths | 1,600 sq.ft. |
$335,000 |
Airbnb cash on cash: 0.16%
|
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. |
$469,000 |
Airbnb cash on cash: -2.1%
|
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. |
$399,000 |
Airbnb cash on cash: -1.37%
|
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: -0.51%
|
9728 S Greenwood AvenueChicago, ILBeautifully updated home featuring 2+2 bedrooms and 2 full baths! This property offers a p... |
2 beds | 2 baths | 891 sq.ft. |
$274,900 |
Airbnb cash on cash: 0.66%
|
9021 S Exchange AvenueChicago, ILSingle Family 4 bedrooms, 1 bath home. Updates in 2019 include kitchen, baths, - ceramic t... |
4 beds | 1 baths | 1,298 sq.ft. |
$125,000 |
Airbnb cash on cash: 5.42%
|
1819 S Michigan Avenue #406Chicago, ILSouth Loop Stunner with Two Private Balconies - Bright and spacious 2BD/2BA with floor-to-... |
2 beds | 2 baths | 1,205 sq.ft. |
$362,000 |
Airbnb cash on cash: -0.96%
|
222 N Columbus Drive #4606Chicago, ILLuxury, convenience and affordability! 46th floor one bedroom at the Park Millenium! Unobs... |
1 beds | 1 baths | 685 sq.ft. |
$279,000 |
Airbnb cash on cash: -0.52%
|
Real Estate investment in Chicago, IL
There are 3,713 properties for sale in the city of Chicago . The median list price in Chicago is $369,000 and the average price per square foot is $213. In November 2025, the average monthly cash on cash return in Chicago is 3.00%. The average monthly rental income in Chicago is $2,342.